Name: 39627-84-4|2-Naphthohydrazide|98%
Brand: Ambeed
SKU: A176952
Price: 19.0 USD
Availability: InStock
Rating: 94 (22 reviews)

1
[ 39627-84-4 ]
[ 555-16-8 ]
LASSBio-1524 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride In ethanol; water at 20℃; for 0.5h;	4.2.1. (E)-N-(4-nitrobenzylidene)-2-naphthohydrazide, (3) 4-Nitrobenzaldehyde (0.17 g; 1.13 mmol) was added to a solution of 2-naphthohydrazide (26) (0.20 g, 1.07 mmol) in absolute ethanol (5 mL) supplemented with two drops of 37% hydrochloric acid. The mixture was stirred at room temperature for 30 min and a precipitate was formed. After the reaction was complete (as assessed by TLC), the mixture was poured into ice, and the precipitate was filtered and dried under vacuum. The desired title compound formed as a pale yellow amorphous solid (0.310 g 90%; Mp 244-246 °C; 1H NMR (300 MHz, DMSO-d6, TMS) δ: 12.24 (s, 1H, NH); 8.58 (s, 1H, Naph-1-H); 8.54 (s, 1H, NCH); 8.28 (d, 3J = 9.0 Hz, 2H, Ph-3-H, Ph-5-H); 8.08-7.97 (m, 6H, Naph-3-H), (-4H, -5H, -8H), Ph-2-H, Ph-6-H); 7.67-7.58 (m, 2H, Naph-6-H, Nap-7-H). 13C NMR (75 MHz, DMSO-d6, TMS) δ: 164.18 (CO); 148.58 (Ph-4-C); 145.99 (NCH); 141.36 (Ph-1-C); 135.12 (Naph-9-C); 132.74 (Naph-2-C); 131.13 (Naph-10-C); 129.62 (Naph-8-C); 128.67 (Naph-1-C, -4C, -6C); 128.37 (Naph-5-C); 127.61 (Naph-7-C); 125.01 (Naph-3-C); 124.72 (Ph-2-C, -3C, -5C, -6C). IR (cm-1, KBr) 3433, 3235 (NH); 1653 (CO); 1536, 1350 (NO2). Anal. Calcd for C18H13N3O3: C: 67.71; H: 4.10; N: 13.16. Found: C: 67.63; H: 4.03; N: 13.26. % purity >99% by HPLC (tR = 5.179 min).
	With ethanol

Reference： [1]Location in patent: experimental part Avila, Carolina M.; Lopes, Alexandra B.; Gonalves, Arlan S.; Da Silva, Leandro L.; Romeiro, Nelilma C.; Miranda, Ana Luisa P.; Sant'Anna, Carlos M.R.; Barreiro, Eliezer J.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1245 - 1253]
[2]Goldstein; Studer [Helvetica Chimica Acta, 1934, vol. 17, p. 1485,1486]

2
[ 2459-25-8 ]
[ 39627-84-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrazine hydrate In ethanol at 55℃; for 0.666667h;	2-naphthohydrazide, 26. A solution of methyl 2-naphthoate (25) (0.400 g, 2.15 mmol), EtOH (5 mL) and hydrazine hydrate 98% (1.72 g, 34.4 mmol) was stirred at 55 oC for 40 minutes and monitored by TLC. After cooling down to room temperature the mixture was poured into ice and the solid filtered to give 0.375 g (94%) of the title compound as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6, TMS) d 9.90 (s, 1H, NH); 8.41 (s, 1H, Nap-1-H); 8.00-7.90 (m, 4H, Nap-3-H, -4H, -5H, -8H); 7.59-7.56 (m, 2H, Nap-6-H, Nap-7-H); 4.54 (s, 2H, NH2).
88%	With hydrazine hydrate In ethanol at 80℃; for 5h;	13.1 First, 5.0 g of methyl 2-naphthoate and 20 mL of ethanol were put in a four-neck flask, and stirred. Then, 5 mL of hydrazine monohydrate (ΝΗ2ΝΗ2·Η20) was added to this mixture, and heated and stirred at 80 °C for 5 hours to be reacted.After the reaction, the solution was added to 100 mL of water, whereby a solid was precipitated. The resulting suspension was subjected to suction filtration to give a solid. This solid was recrystallized from a mixed solvent of chloroform and hexane, so that 4.4 g of 2-naphthohydrazide was prepared as a white solid with a yield of 88 %.The synthetic scheme of Step 1 is shown by (a-12).
88%	With hydrazine hydrate In ethanol at 80℃; for 4h;	General procedure for the preparation of 2-naphthohydrazide (5a) and 5,6,7,8-tetrahydronaphthalene-2-carbohydrazide (5b) General procedure: To a solution of 2.47 mmol (1 eq.) of methyl2-naphthoate (4b) or methyl 5,6,7,8-tetrahydronaphthalene-2-carboxylate (4a) in absoluteEtOH (20 mL) was added 7.73 mL (0.15 mmol, 40 eq.) hydrazine hydrate 80%. The mixturewas refluxed at 80°C for 4 hours. Afterwards, solvent was partially concentrated at reducedpressure and the resulting mixture was poured into ice. The precipitate formed was filtered outand dried under vacuum, producing the desired product.

87%	With hydrazine hydrate In ethanol for 18h; Reflux;
85%	With hydrazine hydrate In ethanol at 160℃; for 1h; Microwave irradiation;
85%	With hydrazine hydrate In ethanol for 4h; Reflux;
82%	With hydrazine hydrate In ethanol at 80℃; for 4h;
80%	With hydrazine hydrate In ethanol at 75℃; for 4h;
80%	With hydrazine hydrate In ethanol Reflux;	General method for the preparation of hydrazides 19a-e General procedure: The appropriate aryl-ester 18a-e (1 eq), was added of EtOH (2.22 ml*mmol/eq) followed by hydrazine monohydrate (3 eq). The solution was refluxed overnight, then cooled to room temperature. The precipitate obtained was filtered and washed with cold EtOH and n-hexane to give the pure product.
72%	With hydrazine hydrate In ethanol Reflux;	4.b b) 2-naphthoquinone hydrazide (4b) 4a (1.54 g, 9 mmol) was dissolved in 30 ml of ethanol, hydrazine hydrate was added, and the reaction was refluxed overnight. The next day, TLC monitored the reaction completely. At room temperature, a yellow solid precipitated continuously. Concentrate to a small volume, ice bath for 30 minutes, and filter to obtain a solid. Drying gave 1.21 g of a yellow solid. Yield: 72%.
71%	With hydrazine hydrate for 5h; Heating;
62%	With hydrazine hydrate In methanol
	With hydrazine hydrate In methanol
	With hydrazine hydrate In ethanol at 20℃; for 24h;
	With hydrazine hydrate at 80℃; for 2h;
	With hydrazine hydrate In ethanol Reflux;
	With hydrazine hydrate In methanol Reflux;

Reference： [1]Avila, Carolina M.; Lopes, Alexandra B.; Gonalves, Arlan S.; Da Silva, Leandro L.; Romeiro, Nelilma C.; Miranda, Ana Luisa P.; Sant'Anna, Carlos M.R.; Barreiro, Eliezer J.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1245 - 1253]
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2011/52516, 2011, A1 Location in patent: Page/Page column 114
[3]Cordeiro, Natália M.; Freitas, Rosana H. C. N.; Fraga, Carlos A. M.; Fernandes, Patricia D. [PLoS ONE, 2016, vol. 11, # 5]
[4]Alves, Marina A.; Chaves, Lorrane S.; Fernandes, Patrícia D.; Fraga, Carlos A. M.; Guerra, Fabiana S.; Rodrigues, Daniel A.; Sagrillo, Fernanda S.; Sant'Anna, Carlos M. R.; Thota, Sreekanth; de Sena M. Pinheiro, Pedro [ChemMedChem, 2020]
[5]Caboni, Laura; Egan, Billy; Kelly, Brendan; Blanco, Fernando; Fayne, Darren; Meegan, Mary J.; Lloyd, David G. [Journal of Chemical Information and Modeling, 2013, vol. 53, # 8, p. 2116 - 2130]
[6]Fu, Jian; Fu, Huixiao; Dieu, Marc; Halloum, Iman; Kremer, Laurent; Xia, Yufen; Pan, Weidong; Vincent, Stéphane P. [Chemical Communications, 2017, vol. 53, # 77, p. 10632 - 10635]
[7]Guedes, Isabella A.; Freitas, Rosana H. C. N.; Cordeiro, Natlia M.; Do Nascimento, Thas S.; Valerio, Tayna S.; Fernandes, Patrcia D.; Dardenne, Laurent E.; Fraga, Carlos A. M. [ChemMedChem, 2016, vol. 11, # 2, p. 234 - 244]
[8]Freitas, Rosana H. C. N.; Cordeiro, Natália M.; Carvalho, Patrícia R.; Alves, Marina A.; Guedes, Isabella A.; Valerio, Tayna S.; Dardenne, Laurent E.; Lima, Lídia M.; Barreiro, Eliezer J.; Fernandes, Patrícia D.; Fraga, Carlos A. M. [Chemical Biology and Drug Design, 2018, vol. 91, # 2, p. 391 - 397]
[9]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]
[10]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN108329232, 2018, A Location in patent: Paragraph 0111; 0112
[11]Khan, Khalid Mohammad; Rasheed, Maimona; Ullah, Zia; Hayat, Safdar; Kaukab, Farhana; Choudhary, M. Iqbal; Ur-Rahman, Atta; Perveen, Shahnaz [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 7, p. 1381 - 1387]
[12]Wu, Dehua; Song, Jintong; Qu, Lang; Zhou, Weilan; Wang, Lei; Zhou, Xiangge; Xiang, Haifeng [Chemistry - An Asian Journal, 2020, vol. 15, # 20, p. 3370 - 3378]
[13]Ono, Katsuhiko; Wakida, Mayuko; Hosokawa, Ryohei; Saito, Katsuhiro; Nishida, Jun-ichi; Yamashita, Yoshiro [Heterocycles, 2007, vol. 72, p. 85 - 90]
[14]Location in patent: scheme or table Lee, Suho; Jung, Kwan-Young; Park, Joohyun; Cho, Joong-Heui; Kim, Yong-Chul; Chang, Sunghoe [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4858 - 4864]
[15]Vechorkin, Oleg; Hirt, Nathalie; Hu, Xile [Organic Letters, 2010, vol. 12, # 15, p. 3567 - 3569]
[16]Yu, Bole; Chen, Ying; Hong, Mei; Duan, Pingping; Gan, Shifeng; Chao, Hui; Zhao, Zujin; Zhao, Jing [Chemical Communications, 2015, vol. 51, # 76, p. 14365 - 14368]
[17]McClure, Jesse J.; Zhang, Cheng; Inks, Elizabeth S.; Peterson, Yuri K.; Li, Jiaying; James Chou [Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9942 - 9959]

3
[ 39627-84-4 ]
[ 3697-66-3 ]
1-[<i>N</i>'-(naphthalene-2-carbonyl)-hydrazinocarbonyl]-cyclopropanecarboxylic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4233 - 4236

4
[ 59043-41-3 ]
[ 39627-84-4 ]
3-(2-naphthyl)-5-[3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl]-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: 3-oxo-3<i>H</i>-spiro[isobenzofuran-1,4'-piperidine]-1'-carbonitrile; 2-naphthohydrazide With ytterbium(III) triflate In toluene at 140℃; for 11h; Stage #2: With sodium hydrogencarbonate In water; toluene	30.2 (2) Preparation of 3-(2-naphthyl)-5-[3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl]-1H-1,2,4-triazole Ytterbium triflate (30 mg, 0.043 mmol) was added to toluene solution (0.5 mL) containing 2-naphthalenecarboxylic acid hydrazide (30 mg, 0.16 mmol) and [3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl]carbonitrile (30 mg, 0.13 mmol), and the mixture was stirred at 140°C for 11 hours in a sealed tube. After saturated aqueous sodium bicarbonate solution was added to the reaction solution, the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was separated and purified by a silica gel column chromatography (Biotage 12M, chloroform:methanol = 40:1) to obtain the title compound (20 mg, 38 %) as a colorless solid.1HNMR(400MHz,DMSO-d6,δppm):1.60-1.86(2H,m),2.22-2.68(2H,m), 3.12-3.60(2H,m),4.02-4.22(2H,m),7.42-8.20(11H,m);mass spectrum(ESI):397(M+H)

Reference： [1]Current Patent Assignee: MERCK & CO INC - EP1566384, 2005, A1 Location in patent: Page/Page column 47-48

5
[ 39627-84-4 ]
[ 447-61-0 ]
N'-{(1E)-[2-(trifluoromethyl)phenyl]-methylene}-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 70℃; for 2h;	4.A 2- (Trifluoromethyl)benzaldehyde (4-B) (135 µL, 1.0 mmol) was added to a partial solution of 2-naphthohydrazide (4-A) (186 mg, 1.0 mmol) in ethanol (4 mL) at 70°C and the mixture stirred at 70°C for 2 h. The mixture was cooled and the thick precipitate was filtered, washed with cold ethanol and dried to give N- ( ( l m- [2-(trifluoromethyl)phenyl] - methylene}-2-naphthohydrazide (4-C).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2005/97759, 2005, A1 Location in patent: Page/Page column 37-38

6
[ 3007-91-8 ]
[ 39627-84-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine hydrate In ethanol Reflux;
85%	With hydrazine hydrate In ethanol Reflux;
0.9 g (48%)	With hydrazine hydrate In ethanol	1 Example 1 STR4 5-Naphthalen-2-yl-3H-[1,3,4]oxadiazole-2-thione To a solution of 2-naphthyl carboxylic acid ethyl ester (2.0 g, 9.99 mmol) in absolute ethanol (30 ml) was added hydrazine hydrate (4.85 ml, 99.9 mmol) and the reaction mixture was heated at reflux temperature for 72 h. The reaction mixture was cooled and the precipitate was filtered off, washed with 96% ethanol (210 ml) and diethyl ether (310 ml), dried in vacuo at 50° C. which afforded 0.9 g (48%) of naphthalene-2-carboxylic acid hydrazide as a solid.

	With hydrazine hydrate In ethanol for 17h; Heating;
	With hydrazine hydrate for 8h; Reflux;
	With hydrazine In ethanol for 16h; Reflux; Inert atmosphere;
	With hydrazine hydrate
	With hydrazine hydrate In ethanol for 3h; Reflux;	4.4. General procedure for the synthesis of 2-naphthoic and 3-phenylpropanoic acid hydrazides (33g and 33h) General procedure: To a solution of the corresponding carboxylic acid derivative (34) or (35) (3 mmol) in 10 mL of ethanol was added a catalytic amount of concentrated H2SO4 and the mixture was refluxed for 2 h, when analysis by TLC indicated the end of the reaction. Then, 3 mL of 80% hydrazine monohydrate was added. The reaction mixture was maintained under reflux for 3 h, when TLC indicated the total consumption of the ester intermediate. The media was poured onto ice and the resulting precipitate was filtered out, affording the corresponding acylhydrazide derivatives (33g) and (33h) as described next.
	With hydrazine hydrate In ethanol Reflux;
	With hydrazine In ethanol at 130℃; for 12h;
	With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube;
	With hydrazine In ethanol at 80℃;
	With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube;	- Route B (R1 = aryl) General procedure: Note: hydrazine and carbon disulphide used during this procedure have to be handled withcaution.The carboxylic compound was first converted into its ethyl ester by refluxing in absoluteethanol in the presence of a few drops of H2SO4. The ester was then treated overnight withhydrazine hydrate (2 to 4 equiv.) without solvent at 120 °C. Evaporation of excess hydrazineyielded the corresponding hydrazide compound. The hydrazide, solubilized in absolute ethanol,was treated with CS2 (5 equiv.) in the presence of KOH (1.7 equiv.) at 85 °C for 3 h. Water wasadded and pH was adjusted to 2-3 with 1N HCl. The formed precipitate was collected byfiltration and washed with water, yielding the 1,3,4-oxadiazol-thione, which was used withoutfurther purification. Finally, the preceding compound was treated with hydrazine hydrate (10equiv.) in absolute ethanol at 100 °C overnight in a sealed tube. After evaporation of excesshydrazine, the residue was purified on a silica gel column to yield the final compound.
	With hydrazine hydrate In ethanol at 100℃; Sealed tube;	General procedure: The ester was then solubilized in EtOH and treated with hydrazine, hydrate (5 equiv.). The mixture was refluxed overnight and solvents were evaporated. Diethyl ether was added and the formed precipitate was filtered and washed with the same solvent to yield the expected hydrazide compound as a powder.

Reference： [1]Kiehl, Jonathan; Hochdörffer, Tim; Carrella, Luca M.; Schünemann, Volker; Nygaard, Mathilde H.; Overgaard, Jacob; Rentschler, Eva [Inorganic Chemistry, 2022, vol. 61, # 7, p. 3141 - 3151]
[2]Location in patent: scheme or table Hu, Yang; Lu, Xiang; Chen, Ke; Yan, Ru; Li, Qing-Shan; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 903 - 909]
[3]Current Patent Assignee: NOVO NORDISK A/S - US5958957, 1999, A
[4]Xu, Zhaowu; Li, Yang; Ma, Xuemei; Gao, Xindong; Tian, He [Tetrahedron, 2008, vol. 64, # 8, p. 1860 - 1867]
[5]Location in patent: scheme or table Ke, Shao-Yong; Qian, Xu-Hong; Liu, Feng-Yi; Wang, Ni; Yang, Qing; Li, Zhong [European Journal of Medicinal Chemistry, 2009, vol. 44, # 5, p. 2113 - 2121]
[6]Location in patent: scheme or table Rai, Ganesha; Kenyon, Victor; Jadhav, Ajit; Schultz, Lena; Armstrong, Michelle; Jameson, J. Brian; Hoobler, Eric; Leister, William; Simeonov, Anton; Holman, Theodore R.; Maloney, David J. [Journal of Medicinal Chemistry, 2010, vol. 53, # 20, p. 7392 - 7404]
[7]Location in patent: scheme or table Ghani, Usman; Ullah, Nisar [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 4042 - 4048] Location in patent: scheme or table Ke, Shaoyong; Liu, Fengyi; Wang, Ni; Yang, Qing; Qian, Xuhong [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 332 - 335]
[8]Location in patent: experimental part Carvalho, Samir A.; Feitosa, Larisse O.; Soares, Marcio; Costa, Thadeu E.M.M.; Henriques, Maria G.; Salomao, Kelly; De Castro, Solange L.; Kaiser, Marcel; Brun, Reto; Wardell, James L.; Wardell, Solange M.S.V.; Trossini, Gustavo H.G.; Andricopulo, Adriano D.; Da Silva, Edson F.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 512 - 521]
[9]Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297]
[10]Harikishore, Amaravadhi; Leow, Min Li; Niang, Makhtar; Rajan, Sreekanth; Pasunooti, Kalyan Kumar; Preiser, Peter Rainer; Liu, Xuewei; Yoon, Ho Sup [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1097 - 1101]
[11]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[12]Khan, Mehebub Ali; Ghosh, Soumen; Bera, Sachinath; Hoque, Anamika; Sk, Ismail; Ansari, Shagufi Naz; Mobin, Shaikh M.; Alam, Md. Akhtarul [Journal of Organic Chemistry, 2020, vol. 85, # 6, p. 4019 - 4025]
[13]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]
[14]Gavara, Laurent; Legru, Alice; Verdirosa, Federica; Sevaille, Laurent; Nauton, Lionel; Corsica, Giuseppina; Mercuri, Paola Sandra; Sannio, Filomena; Feller, Georges; Coulon, Rémi; De Luca, Filomena; Cerboni, Giulia; Tanfoni, Silvia; Chelini, Giulia; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [Bioorganic Chemistry, 2021, vol. 113]

7
[ 39627-84-4 ]
[ 530-62-1 ]
[ 106728-66-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran	4 Example 4 STR7 5-Naphthalen-2-yl-3H-[1,3,4]oxadiazol-2-one To a stirred mixture of naphthalene-2-carboxylic acid hydrazide (2.0 g, 10.7 mmol, prepared as described in example 1) and triethylamine (1.1 g, 10.7 mmol) in dry tetrahydrofuran (40 ml) was added carbonyl diimidazole (2.2 g, 13.4 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and at room temperature for 17 h. The resulting reaction mixture was evaporated in vacuo and to the residue was added water (50 ml) and ethyl acetate (50 ml). The phases were separated and the organic phase was washed with saturated aqueous sodium chloride (2*25 ml), dried (MgSO4) and filtered and evaporated in vacuo affording 2.2 g of crude product which was recrystallized from a mixture of ethyl acetate and heptane 1:1 (60 ml) affording after drying in vacuo at 50° C. 1.2 g (52%) of the title compound as a solid. m.p.: 197-199° C. Calculated for C12 H8 N2 O2: C, 67.92%; H, 3.80%; N, 13.20%. Found C, 67.92%; H, 3.73%; N, 13.04%.

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S - US5958957, 1999, A

8
[ 506-68-3 ]
[ 39627-84-4 ]
5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate In 1,4-dioxane; ethanol; water	3 Example 3 STR6 5-Naphthalen-2-yl-[1,3,4]oxadiazol-2-ylamine To a stirred solution of naphthalene-2-carboxylic acid hydrazide (0.6 g, 3.22 mmol, prepared as described in example 1) in dioxane (20 ml) was added a solution of sodium hydrogen carbonate (0.27 g, 3.22 mmol) in water (15 ml) and the resulting mixture was stirred for 5 min. To the reaction mixture was added cyanogen bromide (0.35 g, 3.3 mmol) and the mixture was stirred for 3 h at room temperature. The precipitate was filtered off and washed with diethyl ether (2*15 ml) and dried in vacuo at 50° C. affording 0.4 g of crude product which was suspended in absolute ethanol (15 ml) and stirred at reflux temperature for 0.5 h. The cooled suspension was filtered and the filter cake was dried in vacuo at 50° C. affording 130 mg (20%) of the title compound as a solid. m.p.: 245-247° C. Calculated for C12 H9 N3 O, 0.1x H2 O: C, 67.66%; H, 4.35%; N, 19.73%. Found C, 67.56%; H, 4.21%; N, 19.84%.

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S - US5958957, 1999, A

9
[ 39627-84-4 ]
[ 79463-77-7 ]
5-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.45 g (51%)	With triethylamine In diethyl ether; water; isopropyl alcohol	12 Example 12 STR15 5-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamide To a stirred solution of naphthalene-2-carboxylic acid hydrazide (0.7 g, 3.76 mmol) in isopropanol (40 ml) was added triethylamine (630 μl, 4.51 mmol) and diphenyl cyanocarbonimidate (0.99 g, 4.14 mmol) and the resulting reaction mixture was stirred at room temperature for 1.5 h. The volatiles were evaporated in vacuo and to the residue was added water (50 ml) and diethyl ether (50 ml). The organic phase was separated and the aqueous phase was acidified to pH=1 with concentrated hydrochloric acid. The precipitate was filtered off and washed with water (310 ml) and diethyl ether (210 ml) and dried in vacuo at 50° C. which afforded 0.45 g (51%) of the title compound as a solid. m.p.: >250° C. Calculated for C13 H10 N4 O: C, 66.10%; H, 3.41%; N, 23.72%. Found C, 65.81%; H, 3.33%; N, 23.54%.

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S - US5958957, 1999, A

10
[ 39627-84-4 ]
[ 335637-29-1 ]
[ 891269-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	308.1 A solution of EDC.HCl (1.4 eq.), HOBt (1.4 eq.) and (2S)-2-[(tert-butoxycarbonyl)amino]-8-oxodecanoic acid in DMF (0.5 M) was premixed at RT for 10 min, and then a solution of 2-naphthohydrazide (1 eq) in DMF (1 M) was added. The mixture was stirred for 16 hr at RT and then it was diluted in DCM, washed with 0.1 M HCl solution and brine. The solution was dried (Na2SO4), concentrated under reduced pressure and the crude product was purified by chromatography on silica gel eluting with 1% MeOH/DCM to obtain the desired hydrazide.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2009/48228, 2009, A1 Location in patent: Page/Page column 83

11
[ 891269-83-3 ]
[ 39627-84-4 ]
[ 891270-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (2S)-8-tert-butoxy-2-[(tert-butoxycarbonyl)amino]-8-oxooctanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-naphthohydrazide In N,N-dimethyl-formamide at 20℃; for 16h;	141.1 A solution of EDC.HCl (1.5 eq.), HOBt (1.5 eq.) and (2S)-8-tert-Butoxy-2-[(tert-butoxycarbonyl)amino]-8-oxooctanoic acid (13, Example 107 Step 3) (1 eq.) in DMF (0.1 M) was premixed at RT for 1 hr, and then 2-naphthohydrazide was added. The mixture was stirred for 16 hr at RT and then concentrated to dryness under reduced pressure. The residue was dissolved in DCM, washed with 1 M HCl solution and brine. The solution was dried (Na2SO4), concentrated under reduced pressure and the resulting brown oil was purified by chromatography on silica gel eluting with 30% EtOAc/petroleum to obtain the hydrazide as a white solid.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2009/48228, 2009, A1 Location in patent: Page/Page column 68

12
[ 56932-61-7 ]
[ 39627-84-4 ]
[ 1048973-56-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic acid In tetrahydrofuran; ethanol at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Diaz, Philippe; Xu, Jijun; Astruc-Diaz, Fanny; Pan, Hao-Min; Brown, David L.; Naguib, Mohamed [Journal of Medicinal Chemistry, 2008, vol. 51, # 16, p. 4932 - 4947]

13
[ 39627-84-4 ]
[ 116096-91-4 ]
[ 1147839-84-6 ]

Yield	Reaction Conditions	Operation in experiment
44.9%	In ethanol at 20℃; for 3h;

Reference： [1]Location in patent: experimental part He, Lingyan; Zhang, Liang; Liu, Xiaofeng; Li, Xianghua; Zheng, Mingyue; Li, HongLin; Yu, Kunqian; Chen, Kaixian; Shen, Xu; Jiang, Hualiang; Liu, Hong [Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2465 - 2481]

14
[ 39627-84-4 ]
[ 139-85-5 ]
[ 1242433-25-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol for 6h; Reflux;
78%	With ammonium cerium (IV) nitrate In ethanol at 65℃; for 3h;

Reference： [1]Fu, Jian; Fu, Huixiao; Dieu, Marc; Halloum, Iman; Kremer, Laurent; Xia, Yufen; Pan, Weidong; Vincent, Stéphane P. [Chemical Communications, 2017, vol. 53, # 77, p. 10632 - 10635]
[2]Lee, Suho; Jung, Kwan-Young; Park, Joohyun; Cho, Joong-Heui; Kim, Yong-Chul; Chang, Sunghoe [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4858 - 4864]

15
[ 39627-84-4 ]
[ 619-66-9 ]
(e)-N'-(4-carboxybenzylidene)-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride In ethanol; water at 20℃; for 0.5h;	(E)-N’-(4-carboxybenzylidene)-2-naphthohydrazide, 22. To a solution of 2-naphthohydrazide (26) (0.200 g, 1.07 mmol) in EtOH (5 mL) containing two drops of 37% hydrochloric acid, 0.169 g (1.13 mmol) of 4-formylbenzoic acid was added. The mixture was stirred at room temperature for 30 minutes, in which we observed extensive precipitation. After detecting the end of the reaction by TLC, the mixture was poured into ice and the precipitate was filtered and dried under vacuum to afford the title compound as a white amorphous solid 0.311 g (91%). Mp > 250 oC. 1H NMR (200 MHz, DMSO-d6, TMS) d: 12.20 (s, 1H, NH); 8.56 (s, 2H, N=CH, Nap-1-H); 8.05-8.02 (m, 6H, Nap-3-H, Nap-4-H, Ph-2-H, (-3H, -5H, -6H); 7.88 (d, 3J = 7.8 Hz, 2H, Nap-5-H, Nap-8-H); 7.66-7.62 (m, 2H, Nap-6-H, Nap-7-H). 13C NMR (50 MHz, DMSO-d6, TMS) d: 167.46 (COOH); 163.91 (CONH); 147.18 (N=CH); 138.95 (Ph-1-C); 134.94 (Nap-9-C); 132.61 (Nap-2-C); 132.27 (Nap-10-C); 131.12 (Ph-4-C); 130.36 (Ph-2-C, -3C, -5C, -6C); 129.49 (Nap-8-C); 128.71 (Nap-1-C); 128.52 (Nap-6-C); 128.25 (Nap-4-C); 127.67 (Nap-5-C); 127.48 (Nap-7-C); 124.85 (Nap-3-C). IR (cm-1, KBr) 3187-2540 (OH); 1690 (C=O, COOH); 1647 (C=O, CONH). Anal. Calcd for C19H14N2O3.H2O: C: 67.85; H: 4.79; N: 8.33. Found: C: 67.88; H: 4.68; N: 7.94. % purity > 95% by HPLC (tR = 3.48 min).

Reference： [1]Avila, Carolina M.; Lopes, Alexandra B.; Gonalves, Arlan S.; Da Silva, Leandro L.; Romeiro, Nelilma C.; Miranda, Ana Luisa P.; Sant'Anna, Carlos M.R.; Barreiro, Eliezer J.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1245 - 1253]

16
[ 39627-84-4 ]
[ 1571-08-0 ]
(E)-N'-(4-(methylcarboxy)benzilidene)-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogenchloride In ethanol; water at 20℃; for 0.5h;	(E)-N'-(4-(methycarboxy)benzilidene)-2-naphthohydrazide, 23. To a solution of (0.177 g, 0.950 mmol) 2-naphthohydrazide (26) in absolute ethanol (4 mL) containing two drops of 37% hydrochloric acid, 0.164 g (0.998 mmol) of methyl 4-formylbenzoate was added. The mixture was stirred at room temperature for 30 minutes, in which we observed extensive precipitation. After detecting the end of the reaction by TLC, the mixture was poured into ice and the precipitate filtered and dried under vacuum to afford the title compound as a white solid 0.241 g (76%). Mp 238-240 oC. 1H NMR (250 MHz, DMSO-d6, TMS) d: 12.20 (s, 1H, NH); 8.54 (s, 2H, Nap-1-H, N=CH); 8.09-8.01 (m, 6H, Nap-3-H, (-4H, -5H, -6H), Ph-3-H, Ph-5-H); 7.88 (d, 3J = 7.5 Hz, 2H, Ph-2-H, Ph-6-H); 7.67-7.61 (m, 2H, Nap-6-H, Nap-7-H); 3.86 (s, 3H, CH3). 13C NMR (62.5 MHz, DMSO-d6, TMS) d: 166.20 (CO2CH3); 163.84 (CONH); 146.71 (N=CH); 139.03 (Ph-1-C); 134.85 (Nap-9-C); 132.49 (Nap-2-C); 130.93 (Nap-10-C); 130.86 (Ph-4-C); 130.12 (Ph-2-C, -3C, -5C, -6C); 129.39 (Nap-8-C); 128.62 (Nap-1-C); 128.44 (Nap-6-C); 128.15 (Nap-4-C); 127.70 (Nap-5-C); 127.40 (Nap-7-C); 124.75 (Nap-3-C); 52.62 (CH3). IR (cm-1, KBr) 3433, 3235 (NH); 1718 (C=O, CO2CH3); 1653 (C=O, CONH). Anal. Calcd for C20H16N2O3: C: 72.28; H: 4.85; N: 8.43. Found: C: 72.04; H: 4.85; N: 8.36. % purity > 99% by HPLC (tR = 5.154 min).

Reference： [1]Avila, Carolina M.; Lopes, Alexandra B.; Gonalves, Arlan S.; Da Silva, Leandro L.; Romeiro, Nelilma C.; Miranda, Ana Luisa P.; Sant'Anna, Carlos M.R.; Barreiro, Eliezer J.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1245 - 1253]

17
[ 2459-25-8 ]
hydrazine monohydrate (NH₂NH_2.H₂O) [ No CAS ]
[ 39627-84-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; water	S.10.1 Step 1: Step 1: Synthesis of 2-naphthohydrazide First, 5.0 g of methyl 2-naphthoate and 20 mL of ethanol were put in a four-neck flask, and stirred. Then, 5 mL of hydrazine monohydrate (NH2NH2.H2O) was added to this mixture, and heated and stirred at 80° C. for 5 hours to be reacted. After the reaction, the solution was added to 100 mL of water, whereby a solid was precipitated. The resulting suspension was subjected to suction filtration to give a solid. This solid was recrystallized from a mixed solvent of chloroform and hexane, so that 4.4 g of 2-naphthohydrazide was prepared as a white solid with a yield of 88%. The synthetic scheme of Step 1 is shown by (a-12).

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2011/101854, 2011, A1

18
[ 39627-84-4 ]
[ 51523-09-2 ]
[ 1297270-50-8 ]

Yield	Reaction Conditions	Operation in experiment
37%	In butan-1-ol at 120℃; for 20h;	14.1 First, 5.7 g of N-[l-(ethylsulfanyl)isobutylidene] aniline, 4.4 g of2- naphthohydrazide, and 40 mL of 1-butanol were put in a 100 mL three-neck flask, and heated and stirred at 120 °C for 20 hours to be reacted. After the reaction, 1-butanol was distilled off to give a brown oily substance. Toluene was added to this oily substance, whereby a solid was precipitated, and then filtrated to give the solid. The resulting solid was recrystallized from toluene, so that 2.7 g of3- isopropyl-5-(2-naphthyl)-4-phenyl-4H-l,2,4-triazole (abbreviation: HiPratz) was prepared as a white solid with a yield of 37 %. The synthetic scheme of Step 1 is shown by (a-13). As described above, the objective compound of Example 14 has a favorable yield.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2011/52516, 2011, A1 Location in patent: Page/Page column 117-118

19
[ 39627-84-4 ]
[ 87876-89-9 ]
[ 1297270-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol at 120℃; for 15h;	13.2 Next, 4.0 g of jV-[l-(ethylsulfanyl)ethylidene] aniline, 4.1 g of 2-naphthohydrazide that was prepared in Step 1 described above, and 60 mL of 1-butanol were put in a 100 mL three-neck flask, and heated and stirred at 120 °C for 15 hours to be reacted. After the reaction, 1-butanol was distilled off to give a brown oily substance. This oily substance was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 1.3 g of 3-methyl-5-(2-naphthyl)-4-phenyl-4H- 1 ,2,4-triazole (abbreviation: HMntz) was prepared as a white solid with a yield of 21 %. The synthetic scheme of Step 2 is shown by (b-12).

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2011/52516, 2011, A1 Location in patent: Page/Page column 114-115

20
[ 3132-99-8 ]
[ 39627-84-4 ]
[ 340228-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol; water for 5h; Reflux;	4.2. General procedure for the Preparation of target compounds 6a-6t General procedure: To a stirred solution of hydrazide 3 (1 mmol) and compound 4 (1 mmol) in ethanol (25 mL), water (5 mL) was added followed by dropwise addition of glacial acetic acid (0.2 mL). The resulting mixture was refluxed for 5 h, after which the solution was poured into ice water. The mixture was stirred until a precipitate formed, which was collected using suction filtration and dried, followed by recrystallization in aqueous methanol.Compounds 6 was synthesized by addition of acetic anhydride (2 mL) to hydrazone 5 (0.2 mmol), and the resulting solution was heated to reflux for 1 h. The reaction mixture was poured into ice water, and the resulting solid product was filtered and washed with copious amounts of water, drying under air.
	In dimethyl sulfoxide at 60℃; for 0.5h;	3.1. General Procedure General procedure: A mixture of aryl aldehyde (1 mmol) and benzhydrazide(1 mmol) was heated at 60 °C for 30 min and then cooled to0 °C. To this mixture, potassium iodide (1.2 mmol) and IBX(1.2 mmol) were added in the DMSO. The resulting solutionwas allowed to stir for 3.5-7.5 h at 25 °C. Upon completion,the mixture was quenched with water and washed withsodium thiosulfate solution and extracted with ethyl acetate.Removal of the solvent followed by purification on silica gelafforded the pure 1,3,4-oxadiazole.

Reference： [1]Location in patent: experimental part Hu, Yang; Lu, Xiang; Chen, Ke; Yan, Ru; Li, Qing-Shan; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 903 - 909]
[2]Khan, P. Rasvan; Durgaprasad; Reddy, S. Gopal; Reddy, G. Raveendra; Hussein, Ibnelwaleed A.; Reddy, B.V. Subba [Letters in Organic Chemistry, 2018, vol. 15, # 1, p. 64 - 69]

21
[ 39627-84-4 ]
[ 6635-20-7 ]
[ 1394115-39-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride In ethanol; water for 1h; Reflux;	4.5. General procedure for the synthesis of NAH derivatives (3-30) General procedure: To a solution of the corresponding hydrazide derivative (33a-33h) (0.829 mmol) in absolute ethanol (90 mL) containing a catalytic amount of 37% aq. hydrochloric acid was added 0.87 mmol of desired aromatic aldehyde derivative. The mixture was stirred at reflux for 60 min, when extensive precipitation was observed. The reaction mixture was then poured into cold water, neutralized with 10% aqueous sodium bicarbonate solution. The precipitate formed was filtered out and dried, furnishing the target compounds in the yields as described next.

Reference： [1]Location in patent: experimental part Carvalho, Samir A.; Feitosa, Larisse O.; Soares, Marcio; Costa, Thadeu E.M.M.; Henriques, Maria G.; Salomao, Kelly; De Castro, Solange L.; Kaiser, Marcel; Brun, Reto; Wardell, James L.; Wardell, Solange M.S.V.; Trossini, Gustavo H.G.; Andricopulo, Adriano D.; Da Silva, Edson F.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 512 - 521]

22
[ 39627-84-4 ]
[ 90-02-8 ]
N'-[(1E)-2-hydroxybenzylidene]-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride In ethanol; water for 1h; Reflux;	4.5. General procedure for the synthesis of NAH derivatives (3-30) General procedure: To a solution of the corresponding hydrazide derivative (33a-33h) (0.829 mmol) in absolute ethanol (90 mL) containing a catalytic amount of 37% aq. hydrochloric acid was added 0.87 mmol of desired aromatic aldehyde derivative. The mixture was stirred at reflux for 60 min, when extensive precipitation was observed. The reaction mixture was then poured into cold water, neutralized with 10% aqueous sodium bicarbonate solution. The precipitate formed was filtered out and dried, furnishing the target compounds in the yields as described next.

Reference： [1]Location in patent: experimental part Carvalho, Samir A.; Feitosa, Larisse O.; Soares, Marcio; Costa, Thadeu E.M.M.; Henriques, Maria G.; Salomao, Kelly; De Castro, Solange L.; Kaiser, Marcel; Brun, Reto; Wardell, James L.; Wardell, Solange M.S.V.; Trossini, Gustavo H.G.; Andricopulo, Adriano D.; Da Silva, Edson F.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 512 - 521]

23
[ 40079-92-3 ]
[ 39627-84-4 ]
1-napthoic acid N'-(adamantane-1-carbonyl)hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In acetonitrile at 0 - 20℃; for 6h;

Reference： [1]Harikishore, Amaravadhi; Leow, Min Li; Niang, Makhtar; Rajan, Sreekanth; Pasunooti, Kalyan Kumar; Preiser, Peter Rainer; Liu, Xuewei; Yoon, Ho Sup [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1097 - 1101]

24
[ 100-42-5 ]
[ 39627-84-4 ]
(E)-2-styrylnaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 2-naphthohydrazide With copper(l) iodide; toluene-4-sulfonic acid; palladium dichloride In dimethyl sulfoxide; acetonitrile at 20℃; for 1h; Stage #2: styrene In dimethyl sulfoxide; acetonitrile at 100℃; for 3h; stereoselective reaction;

Reference： [1]Zhang, Yong-Gang; Liu, Xiang-Lei; He, Zeng-Yang; Li, Xi-Ming; Kang, Hong-Jian; Tian, Shi-Kai [Chemistry - A European Journal, 2014, vol. 20, # 10, p. 2765 - 2769]

25
[ 39627-84-4 ]
[ 100-52-7 ]
[ 967-72-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 2-naphthohydrazide; benzaldehyde In N,N-dimethyl-formamide at 60℃; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine; eosin y In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation; Inert atmosphere;	General Procedure for the synthesis of 2,5-disubtituted 1,3,4-oxadiazoles 3 from aldehydes and acylhydrazides General procedure: Asolution of an aldehyde 1 (1.0 mmol)and an acylhydrazide 2 (1.0 mmol) inDMF (3 mL) was heated at 60 oCfor 2-4 h to form the corresponding acylhydrazone (as monitored by TLC). Then,eosin Y (2.0 mol%) and iPr2NEt (2.0 equiv.) were addedand the mixture was irradiated with green LEDs (2.6 W, 161 lm) with stirringunder an air atmosphere at rt for 12-20 h. After completion of the reaction(monitored by TLC), water (5 mL) was added and the mixture was extracted withEtOAc (3 × 5 mL). The combined organic phase was dried over MgSO4,filtered and evaporated under reduced pressure. The resulting product waspurified by silica gel column chromatography using a gradient mixture ofhexane/ethyl acetate as eluent to afford an analytically pure sample of 3. All the products are known compoundsand were characterized by the comparison of their spectral data with thosereported in the literature

Reference： [1]Yadav, Arvind K.; Yadav, Lal Dhar S. [Tetrahedron Letters, 2014, vol. 55, # 13, p. 2065 - 2069]

26
[ 39627-84-4 ]
[ 100-06-1 ]
[ 1236115-17-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 1-(4-methoxyphenyl)ethanone With iodine; dimethyl sulfoxide In water at 110℃; for 1h; Sealed tube; Stage #2: 2-naphthohydrazide With potassium carbonate In water; dimethyl sulfoxide at 110℃; for 15h; Sealed tube;

Reference： [1]Gao, Qinghe; Liu, Shan; Wu, Xia; Zhang, Jingjing; Wu, Anxin [Organic Letters, 2015, vol. 17, # 12, p. 2960 - 2963]

27
[ 39627-84-4 ]
[ 100-52-7 ]
C₁₈H₁₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid In ethanol Reflux;	EXPERIMENTAL General procedure: The following reagents and solvents were used: tintetrachloride (special purity grade, ρ = 2.03 g/mL); hydrazides of benzoic, 2-naphthoic, 2-hydroxybenzoic, and 3-hydroxy-2-naphthoic acids (chemical purity grade); benzaldehyde (pure grade); methanol, acetonitrile, DMF, diethyl ether (special purity grade). Benzaldehyde R-benzoyl(naphthoyl)hydrazones (2-RHBb and 3-RHLb, respectively, where R = H, OH) were synthesized through condensation of benzaldehyde and acid hydrazides by the general procedure reported in [6]. An equimolar amount ofthe aldehyde (in the presence of catalytic amounts of acetic acid) was added to saturated solutions of 0.1 mol of hydrazides in ethanol, and the reaction mixture was heated under reflux until the formation of precipitates (15-30 min), which were recrystallized from acetonitrile. The yield, % (mp, °), was: 76 (210), 86 (256), 90 (170), and 85 (210) for HBb, 2-OH-HBb, HLb,and 3-OH-HLb, respectively. The purity of hydrazones was monitored by TLC on Silufol UV254 plates in the chloroform : methanol = 20 : 1 eluent.

Reference： [1]Shmatkova; Seifullina; Korlyukov [Russian Journal of Inorganic Chemistry, 2015, vol. 60, # 9, p. 1068 - 1073][Zh. Neorg. Khim., 2015, vol. 60, # 9, p. 1175 - 1180,5]

28
[ 2243-83-6 ]
[ 39627-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2 h / 20 °C 2: hydrazine hydrate / ethanol / 4 h / 80 °C
	Multi-step reaction with 2 steps 1: 2 h / 20 °C 2: hydrazine hydrate / ethanol / 4 h / 80 °C
	Multi-step reaction with 2 steps 1: 2 h / 20 °C 2: hydrazine hydrate / ethanol / 4 h / 75 °C

	With hydrazine hydrate In dichloromethane at 0 - 20℃; for 12h;
	With dmap; triethylamine; hydrazine In dichloromethane at 20℃; for 0.5h;

Reference： [1]Guedes, Isabella A.; Freitas, Rosana H. C. N.; Cordeiro, Natlia M.; Do Nascimento, Thas S.; Valerio, Tayna S.; Fernandes, Patrcia D.; Dardenne, Laurent E.; Fraga, Carlos A. M. [ChemMedChem, 2016, vol. 11, # 2, p. 234 - 244]
[2]Cordeiro, Natália M.; Freitas, Rosana H. C. N.; Fraga, Carlos A. M.; Fernandes, Patricia D. [PLoS ONE, 2016, vol. 11, # 5]
[3]Freitas, Rosana H. C. N.; Cordeiro, Natália M.; Carvalho, Patrícia R.; Alves, Marina A.; Guedes, Isabella A.; Valerio, Tayna S.; Dardenne, Laurent E.; Lima, Lídia M.; Barreiro, Eliezer J.; Fernandes, Patrícia D.; Fraga, Carlos A. M. [Chemical Biology and Drug Design, 2018, vol. 91, # 2, p. 391 - 397]
[4]Deshmukh, Dewal S.; Gangwar, Neha; Bhanage, Bhalchandra M. [European Journal of Organic Chemistry, 2019, vol. 2019, # 18, p. 2919 - 2927]
[5]Zhao, Yating; Shi, Chengcheng; Su, Xing; Xia, Wujiong [Chemical Communications, 2020, vol. 56, # 39, p. 5259 - 5262]

29
[ 39627-84-4 ]
[ 87199-17-5 ]
(E)-N-(4-boronic acid benzylidene)naphthalene-2-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride In ethanol; water at 20℃; for 3h;	General procedure for the preparation of N-acylhydrazone derivatives (2a-c) General procedure: To a solutionof 1.61 mmol (1 eq.) of 2-naphthohydrazide (8) or 5,6,7,8-tetrahydronaphthalene-2-carbohydrazide(5) in absolute EtOH (20 mL) containing two drops of solution hydrochloric acid10%, was added 1.7 mmol (1 eq.) of the corresponding aromatic aldehyde. The mixture was stirred at room temperature for 3 hours. Afterwards, the solvent was partially concentrated atreduced pressure and the resulting mixture was poured into ice. The precipitate formed was filteredout and dried under vacuum, producing the desired N-acylhydrazone in high yield.(E)-N-(4-nitrobenzylidene)-5,6,7,8-tetrahydronaphthalene-2-carbohydrazide (2a, LASSBio-1764). Beige powder purified by recrystallized from ethanol, 94%, 1H-NMR (200 MHz,DMSO-d6): δ 1.76 (4H, sl); 2.78 (4H, sl); 7.21 (1H, d, J = 8 Hz); 7.64 (2H, sl); 8.00 (2H, m); 8.33(2H, d, J = 10 Hz); 8.53 (1H, s); 12.04 (1H, s) (S8 Fig). 13C-NMR (50 MHz, DMSO-d6) δ 22.5;28.8; 124.1; 124.8; 128.0; 128.4; 129.2; 130.1; 137.0; 140.8; 141.4; 145.0; 147.8; 163.5 (S9 Fig). IR(KBr) cm-1: 1314 e 1519 ( N-O); 1652 ( C = O), 3231 ( N-H). % of purity >99% by HPLC.

Reference： [1]Cordeiro, Natália M.; Freitas, Rosana H. C. N.; Fraga, Carlos A. M.; Fernandes, Patricia D. [PLoS ONE, 2016, vol. 11, # 5]

30
[ 100-42-5 ]
[ 39627-84-4 ]
[ 1236115-17-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: styrene With iodine; oxygen In dimethyl sulfoxide at 120℃; for 6h; Stage #2: 2-naphthohydrazide With oxygen; potassium carbonate In dimethyl sulfoxide at 120℃; for 2h;

Reference： [1]Fan, Yuxing; He, Yongqin; Liu, Xingxing; Hu, Ting; Ma, Haojie; Yang, Xiaodong; Luo, Xinliang; Huang, Guosheng [Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6820 - 6825]

31
[ 39627-84-4 ]
[ 536-74-3 ]
[ 1236115-17-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: phenylacetylene With iodine; oxygen In dimethyl sulfoxide at 120℃; for 6h; Stage #2: 2-naphthohydrazide With oxygen; potassium carbonate In dimethyl sulfoxide at 120℃; for 2h;

Reference： [1]Fan, Yuxing; He, Yongqin; Liu, Xingxing; Hu, Ting; Ma, Haojie; Yang, Xiaodong; Luo, Xinliang; Huang, Guosheng [Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6820 - 6825]

32
[ 120-72-9 ]
[ 39627-84-4 ]
[ 23746-81-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With copper(l) iodide; oxygen; toluene-4-sulfonic acid; palladium dichloride In nitromethane; dimethyl sulfoxide at 100℃; for 10h;

Reference： [1]Liu, Congrong; Yang, Fulai [Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1213 - 1217]

33
[ 75-15-0 ]
[ 39627-84-4 ]
5-(naphthalen-2-yl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In ethanol at 85℃; for 3h;
	With potassium hydroxide In ethanol at 85℃; for 3h;	- Route B (R1 = aryl) General procedure: Note: hydrazine and carbon disulphide used during this procedure have to be handled withcaution.The carboxylic compound was first converted into its ethyl ester by refluxing in absoluteethanol in the presence of a few drops of H2SO4. The ester was then treated overnight withhydrazine hydrate (2 to 4 equiv.) without solvent at 120 °C. Evaporation of excess hydrazineyielded the corresponding hydrazide compound. The hydrazide, solubilized in absolute ethanol,was treated with CS2 (5 equiv.) in the presence of KOH (1.7 equiv.) at 85 °C for 3 h. Water wasadded and pH was adjusted to 2-3 with 1N HCl. The formed precipitate was collected byfiltration and washed with water, yielding the 1,3,4-oxadiazol-thione, which was used withoutfurther purification. Finally, the preceding compound was treated with hydrazine hydrate (10equiv.) in absolute ethanol at 100 °C overnight in a sealed tube. After evaporation of excesshydrazine, the residue was purified on a silica gel column to yield the final compound.

Reference： [1]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[2]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]

34
[ 39627-84-4 ]
[ 99163-12-9 ]
(E)-N'-(4-(pyridin-4-yl)benzylidene)-2-naphthohydrazide [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 91,p. 391 - 397

35
[ 3029-19-4 ]
[ 39627-84-4 ]
naphthalene-2-carboxylic acid pyren-1-ylmethylene-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol at 50℃; for 2h;	2.5.1. Compound 1: Synthesis of 3-hydroxy-naphthalene-2-carboxylic Acid Pyren-1-ylmethylene-hydrazide (Compound 1) General procedure: Compound 3-hydroxy-naphthalene-2-carboxylic acid hydrazide (1.5 mmol, 0.30 g) has been treated with 1-pyrene carboxaldehyde (1.5 mmol, 0.20 g) in methanol at 50 °C for 2 h. to form a yellow solid. The product thus obtained has been filtered and then dried under vacuum (yield: 0.35 g, 76%).

Reference： [1]Ghosh, Soumen; Khan, Mehebub Ali; Ganguly, Aniruddha; Masum, Abdulla Al; Alam, Md. Akhtarul; Guchhait, Nikhil [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 190, p. 471 - 477]

36
[ 39627-84-4 ]
[ 52211-82-2 ]
N’-(4-hydroxybenzylidene)-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	In ethanol for 24h; Reflux;	General method for the preparation of N'-phenyllidene-2-bycyclo-hydrazides 20a-e, 21a-e, 22a-e, 23a-e General procedure: A mixture of the appropriate aryl-hydrazide 19a-e (1 eq) and the appropriately substituted benzaldehyde or acetophenone (1.2 eq) in EtOH (8.5 ml . mmol/eq) was refluxed overnight. The reaction was then allowed to cool to room temperature. The precipitate formed was collected by filtration and washed with cold EtOH and n-hexane. The solid obtained was purified by recrystallisation to give the pure title compound.

Reference： [1]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

37
[ 39627-84-4 ]
(3,4-diethoxybenzylidene)hydrazine [ No CAS ]
N’-(3,4-diethoxybenzylidene)-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol for 24h; Reflux;	General method for the preparation of N'-phenyllidene-2-bycyclo-hydrazides 20a-e, 21a-e, 22a-e, 23a-e General procedure: A mixture of the appropriate aryl-hydrazide 19a-e (1 eq) and the appropriately substituted benzaldehyde or acetophenone (1.2 eq) in EtOH (8.5 ml . mmol/eq) was refluxed overnight. The reaction was then allowed to cool to room temperature. The precipitate formed was collected by filtration and washed with cold EtOH and n-hexane. The solid obtained was purified by recrystallisation to give the pure title compound.

Reference： [1]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

38
[ 39627-84-4 ]
[ 52693-87-5 ]
[ 359605-76-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	In ethanol for 24h; Reflux;	General method for the preparation of N'-phenyllidene-2-bycyclo-hydrazides 20a-e, 21a-e, 22a-e, 23a-e General procedure: A mixture of the appropriate aryl-hydrazide 19a-e (1 eq) and the appropriately substituted benzaldehyde or acetophenone (1.2 eq) in EtOH (8.5 ml . mmol/eq) was refluxed overnight. The reaction was then allowed to cool to room temperature. The precipitate formed was collected by filtration and washed with cold EtOH and n-hexane. The solid obtained was purified by recrystallisation to give the pure title compound.

Reference： [1]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

39
[ 39627-84-4 ]
(1-(4-cyclohexylphenyl)ethylidene)hydrazine [ No CAS ]
N’-(1-(4-cyclohexylphenyl)ethylidene)-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol for 24h; Reflux;	General method for the preparation of N'-phenyllidene-2-bycyclo-hydrazides 20a-e, 21a-e, 22a-e, 23a-e General procedure: A mixture of the appropriate aryl-hydrazide 19a-e (1 eq) and the appropriately substituted benzaldehyde or acetophenone (1.2 eq) in EtOH (8.5 ml . mmol/eq) was refluxed overnight. The reaction was then allowed to cool to room temperature. The precipitate formed was collected by filtration and washed with cold EtOH and n-hexane. The solid obtained was purified by recrystallisation to give the pure title compound.

Reference： [1]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

40
[ 434-45-7 ]
[ 39627-84-4 ]
[ 17435-72-2 ]
N-(4-methylene-5-oxo-2-phenyl-2-(trifluoromethyl)pyrrolidin-1-yl)-2-naphthamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 2,2,2-Trifluoroacetophenone; 2-naphthohydrazide With toluene-4-sulfonic acid In 1,4-dioxane Reflux; Stage #2: ethyl 2-bromomethyl-2-propenoate With tin In 1,4-dioxane Reflux;	5-Trifluoromethyl-5-aryl-3-methylidenepyrrolidin-2-ones (4); General Procedure General procedure: Trifluoromethyl ketones (1; 0.30 mmol, 1 equiv), acylhydrazines (2; 0.45 mmol, 1.5 equiv) and TsOH (20 mol%) were added to a dried round-bottom flask (50 mL) fitted with a magnetic bar. 1,4-Dioxane 4 mL) was then added and the mixture was stirred and heated to reflux. After the formation of acylhydrazones (monitored by TLC), tin powder (1.35 mmol, 4.5 equiv) and ethyl 2-(bromomethyl)acrylate (3; 1.20 mmol, 4 equiv) were added to the flask. When acylhydrazones had essentially disappeared (monitored by TLC), the reaction mixture was cooled to r.t., then 1,4-dioxane was removed under vacuum. Saturated NH4Cl solution (10 mL) was added and the mixture was stirred for 10 min. The mixture was extracted with EtOAc (3 × 10 mL) and the combined organic phases were dried (MgSO4) and concentrated. Purification of the residue by silica gel column chromatography (petroleum ether-EtOAc, 4:1) furnished the pure products 4.

Reference： [1]Wang, Ke-Hu; Wang, Jianglong; Wang, Yalin; Su, Yingpeng; Huang, Danfeng; Fu, Ying; Du, Zhengyin; Hu, Yulai [Synthesis, 2018, vol. 50, # 9, p. 1907 - 1913]

41
[ 39627-84-4 ]
[ 123-54-6 ]
(3,5-Dimethyl-1H-pyrazol-1-yl) (naphthalen-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: acetylacetone With piperidine at 20℃; Stage #2: 2-naphthohydrazide for 0.166667h;	5 4.1.1 General procedure for the preparation of (substituted phenyl) (3,5-dimethyl-1H-pyrazol-1-yl) methanone derivatives (3a-3o), (4a-c) and (5a-b) General procedure: A mixture containing acetyl acetone, 3-chloro-2,4-pentanedione, 3-aryloxy-2,4-pentanediones and ethyl acetoacetate was ground in the presence of piperidine as a catalyst. The reaction was carried out in a glass mortar and pestle at room temperature. After grinding for 5-10min, hydrazine hydrate or suitable aryl hydrazines (1mmol) was added, and the grinding was continued for further 10min. The progress of the reaction was monitored by TLC using n-hexane/ethyl acetate (8:2). On completion, the reaction mixture was diluted with ethyl acetate and filtered to remove salts, and the filtrate was concentrated. Recrystallization from ethanol afforded pure products (3a-3o), (4a-c) [38] and (5a-b).

Reference： [1]Channar, Pervaiz Ali; Afzal, Saira; Ejaz, Syeda Abida; Saeed, Aamer; Larik, Fayaz Ali; Mahesar, Parvez Ali; Lecka, Joanna; Sévigny, Jean; Erben, Mauricio F.; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2018, vol. 156, p. 461 - 478]

42
[ 39627-84-4 ]
[ 1694-29-7 ]
(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl) (naphthalen-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-chloropentane-2,4-dione With piperidine at 20℃; Stage #2: 2-naphthohydrazide for 0.166667h;	13 4.1.1 General procedure for the preparation of (substituted phenyl) (3,5-dimethyl-1H-pyrazol-1-yl) methanone derivatives (3a-3o), (4a-c) and (5a-b) General procedure: A mixture containing acetyl acetone, 3-chloro-2,4-pentanedione, 3-aryloxy-2,4-pentanediones and ethyl acetoacetate was ground in the presence of piperidine as a catalyst. The reaction was carried out in a glass mortar and pestle at room temperature. After grinding for 5-10min, hydrazine hydrate or suitable aryl hydrazines (1mmol) was added, and the grinding was continued for further 10min. The progress of the reaction was monitored by TLC using n-hexane/ethyl acetate (8:2). On completion, the reaction mixture was diluted with ethyl acetate and filtered to remove salts, and the filtrate was concentrated. Recrystallization from ethanol afforded pure products (3a-3o), (4a-c) [38] and (5a-b).

Reference： [1]Channar, Pervaiz Ali; Afzal, Saira; Ejaz, Syeda Abida; Saeed, Aamer; Larik, Fayaz Ali; Mahesar, Parvez Ali; Lecka, Joanna; Sévigny, Jean; Erben, Mauricio F.; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2018, vol. 156, p. 461 - 478]

43
[ 39627-84-4 ]
[ 933-88-0 ]
2-methylbenzoic acid N'-(naphthalene-2-carbonyl)hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.2%	With sodium carbonate In tetrahydrofuran; water at 20℃; Cooling with ice;	9 4b (121mg, 0.65mmol) was placed in a bottle, dissolved in a mixed solvent of THF/H2O (4/1), and sodium carbonate solid was added as an acid binding agent.Under ice bath, a solution of o-methylbenzoyl chloride in THF was added dropwise, the ice bath was removed, and the reaction was stirred at room temperature overnight. The next day, TLC detected the reaction completely. The reaction was stopped, and the reaction mixture was concentrated to dryness. EtOAc was evaporated. A white solid 93.4 mg was obtained. Yield: 47.2%.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN108329232, 2018, A Location in patent: Paragraph 0131; 0132

44
[ 39627-84-4 ]
[ 329-15-7 ]
4-trifluoromethylbenzoic acid N'-(naphthalene-2-carbonyl)hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.3%	With sodium carbonate In tetrahydrofuran; water at 20℃; Cooling with ice;	6 Example 6: 4-Trifluoromethyl-benzoic acid-N'-(naphthalene-2-carbonyl)-hydrazide (Compound 6) 4b (121mg, 0.65mmol) was placed in a bottle, dissolved in a mixed solvent of THF/H2O (4/1), sodium carbonate solid was added as an acid binding agent, and 4-trifluoromethylbenzene was added dropwise under ice bath conditions. A solution of formyl chloride in THF was removed from the ice bath and the reaction was stirred at room temperature overnight. The next day, TLC detected the reaction completely. The reaction was quenched, and the reaction mixture was evaporated to dryness. Column chromatography gave 152.1 mg of a white solid. Yield: 65.3%.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN108329232, 2018, A Location in patent: Paragraph 0119; 0120

45
[ 39627-84-4 ]
[ 874-60-2 ]
4-methylbenzoic acid-N'-(naphthalene-2-carbonyl)hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.9%	With sodium carbonate In tetrahydrofuran; water at 20℃; Cooling with ice;	4.c c) 4-methyl-benzoic acid-N'-(naphthalene-2-carbonyl)-hydrazide (Compound 4) 4b (121 mg, 0.65 mmol) was placed in a bottle, dissolved in a mixed solvent of THF/H2O (4/1), and sodium carbonate solid was added as an acid binding agent. A solution of p-methylbenzoyl chloride in THF was added dropwise under ice-cooling, the ice bath was removed, and the reaction was stirred at room temperature overnight. The next day, TLC detected the reaction completely. The reaction was quenched, and the reaction mixture was evaporated to dryness. Column chromatography gave 108 mg of a white solid. Yield: 54.9%.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN108329232, 2018, A Location in patent: Paragraph 0113; 0114

46
[ 39627-84-4 ]
[ 2719-27-9 ]
cyclohexanecarboxylic acid N'-(naphthalene-2-carbonyl)hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.2%	With sodium carbonate In tetrahydrofuran; water at 20℃; Cooling with ice;	7 Example 7: cyclohexanecarboxylic acid-N'-(naphthalene-2-carbonyl)-hydrazide (Compound 7) 4b (121 mg, 0.65 mmol) was placed in a bottle and dissolved in a mixed solvent of THF/H2O (4/1).Sodium carbonate solid was added as an acid binding agent, and a solution of cyclohexanecarboxylic acid chloride in THF was added dropwise under ice bath, the ice bath was removed, and the reaction was stirred at room temperature overnight. The next day, TLC detected the reaction completely. The reaction was stopped, and the reaction mixture was concentrated to dryness.The filtrate was concentrated to dryness and column chromatography. A white solid was obtained in 110.2 mg. Yield: 57.2%.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN108329232, 2018, A Location in patent: Paragraph 0122; 0123

47
[ 39627-84-4 ]
[ 4559-70-0 ]
[ 28402-08-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium persulfate; palladium diacetate; benzenesulfonic acid; bis-diphenylphosphinomethane In N,N-dimethyl acetamide; dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Schlenk technique;

Reference： [1]Dong, Jianyu; Liu, Long; Ji, Xuyu; Shang, Qian; Liu, Lixin; Su, Lebin; Chen, Bing; Kan, Ruifeng; Zhou, Yongbo; Yin, Shuang-Feng; Han, Li-Biao [Organic Letters, 2019, vol. 21, # 9, p. 3198 - 3203]

48
[ 4521-33-9 ]
[ 39627-84-4 ]
(E)-N′-((5-nitrothiophen-2-yl)methylene)-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With acetic acid; In methanol; for 6h;Reflux;	General procedure: The receptors R1-R4 were prepared by a simple Schiff base condensationreaction between 5-nitrothiophene-2-carbaldehyde (0.17 g,1.10 mmol) and different substituted hydrazide, such as 4-nitrobenzohydrazide(0.2 g, 1.10 mmol), 2-naptho-hydrazide (0.1 g,0.53 mmol), 4-methyl-benzohydrazide (0.1 g, 0.66 mmol), benzohydrazide(0.1 g, 0.73 mmol) as depicted in Scheme 2, and were dissolvedin 5mL ofmethanol solution. To this, a catalytic amount of aceticacid was added (3?4 drops) and the mixture was refluxed for 6 h. Thefinal solid products were collected, filtered, and washed thoroughlywith methanol. The final products were confirmed through TLC by theappearance of a single spot.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 219,p. 517 - 529

49
[ 39627-84-4 ]
3-fluoro-4-(α-D-mannopyranosyloxy)benzaldehyde [ No CAS ]
(E)-N'-[3-fluoro-4-(α-D-mannopyranosyloxy)benzylidene]-2-naphthohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With acetic acid In water; acetonitrile at 20℃;	General procedure A for acylhydrazone formation General procedure: flask was charged with a magnetic stirrer, then aldehyde 121 and hydrazide 2a,c-e,g-h,j-t were dissolved in H2O/MeCN (2 mL, 7:3). AcOH (100 μL) was added and the mixture was stirred at r.t. for 5-22 h until only product was detected by MS. Then, the mixture was neutralized with 1 M aq. NaOH and the solvents were removed under reduced pressure. The residue was purified by MPLC on RP-18 (H2O/MeCN, 5:95 to 20:80) to give the desired products 3a,c-e,g-h,j-t. For synthesis of 3b, 3f, 3i and3u, please see reference 21.

Reference： [1]Frei, Priska; Silbermann, Marleen; Mühlethaler, Tobias; Jiang, Xiaohua; Schwardt, Oliver; Hevey, Rachel; Ernst, Beat [Arkivoc, 2019, vol. 2019, # 4, p. 143 - 167]

50
[ 5470-96-2 ]
[ 39627-84-4 ]
2-(naphthalen-2-yl)-5-(quinolin-2-yl)-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dimethyl sulfoxide at 110℃; Sealed tube;	Standard procedure for the synthesis of 5-(quinolin-2-yl)-1,3,4-oxadiazoles General procedure: A 25 mL pressure vial was charged with 2-methylquinoline (1a) (71.5 mg, 0.50 mmol, 1.0 equiv.), I2 (317.3 mg, 1.25 mmol, 2.5 equiv.) and DMSO (3.0 mL). The vial was sealed and the resulting mixture was stirred at 110 °C for 4-6 h under an air atmosphere, after disappearance of the reactant (monitored by TLC), then added benzohydrazide (2a) (81.6 mg, 0.6 mmol, 1.2 equiv.) , K2CO3 (414.0 mg, 3.0 mmol, 6.0 equiv.) at 110 °C for another 4-6 h. After the reaction completed, and added 50 mL water to the mixture, then extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% Na2S2O3 solution (w/w), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by flash column chromatography on silica gel to yield the corresponding product 3aa as a yellow solid (72% yield).

Reference： [1]Shang, Zhi-Hao; Sun, Ji-Na; Guo, Jiang-Shan; Sun, Yuan-Yuan; Weng, Wei-Zhao; Zhang, Zhen-Xiao; Li, Zeng-Jing; Zhu, Yan-Ping [Tetrahedron, 2020, vol. 76, # 6]

51
[ 39627-84-4 ]
4-formyl-N-hydroxybenzamide [ No CAS ]
(E)-4-((2-(2-naphthoyl)hydrazono)methyl)-N-hydroxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogenchloride In ethanol; water at 20℃; for 2h;

Reference： [1]Alves, Marina A.; Chaves, Lorrane S.; Fernandes, Patrícia D.; Fraga, Carlos A. M.; Guerra, Fabiana S.; Rodrigues, Daniel A.; Sagrillo, Fernanda S.; Sant'Anna, Carlos M. R.; Thota, Sreekanth; de Sena M. Pinheiro, Pedro [ChemMedChem, 2020]

52
[ 39627-84-4 ]
[ 492-88-6 ]
C₂₀H₁₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In ethanol	2.2. Synthesis of ligands (H2L1-4) General procedure: Substituted aryl hydrazone ligands H2L1-3 were prepared by thecondensation of 3-ethoxy-2-hydroxybenzaldehyde (1.0 mmol) with the corresponding hydrazides (1.0 mmol) [1-naphthoichydrazide (H2L1), 2-furoic hydrazide (H2L2) and 2-thiophenecarboxylicacid hydrazide (H2L3)], while, H2L4 was obtained by thecondensation of 2-hydroxy-1-naphthaldehyde with isonicotinichydrazide in equimolar ratio (1.0 mmol, each) in EtOH mediumby following standard procedures [15,56,65]. The resulting compoundswere then filtered, washed thoroughly with ethanol anddried over fused CaCl2 in a desiccator. Elemental analysis resultsNMR (1H and 13C), UV-Vis and IR data verified their preparation.

Reference： [1]Dinda, Rupam; Panda, Arpita; Banerjee, Atanu; Mohanty, Monalisa; Pasayat, Sagarika; Tiekink, Edward R.T. [Polyhedron, 2020, vol. 183]

53
[ 39627-84-4 ]
[ 17754-90-4 ]
2-naphthoic hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol for 3h; Reflux;	2.2. Synthesis of ligands (H2L1-3) General procedure: The hydrazone ligands (H2L1-3) were synthesized by the reported method [10]. Briefly, an equimolar ratio of 4-(diethylamino)-2-hydroxybenzaldehyde and respective acid hydrazides (1-naphthoic hydrazide=H2L1, 2-naphthoic hydrazide=H2L2, and 3-hydroxy-2-naphthoic hydrazide=H2L3 were dissolved in ethanol and the mixture was refluxed for 3h. A yellowish solid was precipitated, filtered, washed with ethanol and finally dried over fused CaCl2. The structure of the synthesized ligands were confirmed by elemental analysis, NMR (1H and 13C) and IR spectroscopy (Scheme 1 ).
78%	In ethanol for 3h; Reflux;	2.2. Synthesis of ligands (H2L1-3) General procedure: The hydrazone ligands (H2L1-3) were synthesized by the reported method [10]. Briefly, an equimolar ratio of 4-(diethylamino)-2-hydroxybenzaldehyde and respective acid hydrazides (1-naphthoic hydrazide=H2L1, 2-naphthoic hydrazide=H2L2, and 3-hydroxy-2-naphthoic hydrazide=H2L3 were dissolved in ethanol and the mixture was refluxed for 3h. A yellowish solid was precipitated, filtered, washed with ethanol and finally dried over fused CaCl2. The structure of the synthesized ligands were confirmed by elemental analysis, NMR (1H and 13C) and IR spectroscopy (Scheme 1 ).

Reference： [1]Banerjee, Atanu; Dinda, Rupam; Garribba, Eugenio; Lima, Sudhir; Patra, Sushree Aradhana; Sahu, Gurunath; Sahu, Kausik; Sasamori, Takahiro; Sciortino, Giuseppe [Journal of Inorganic Biochemistry, 2022, vol. 233]
[2]Banerjee, Atanu; Dinda, Rupam; Garribba, Eugenio; Lima, Sudhir; Patra, Sushree Aradhana; Sahu, Gurunath; Sahu, Kausik; Sasamori, Takahiro; Sciortino, Giuseppe [Journal of Inorganic Biochemistry, 2022, vol. 233]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	39627-84-4	MDL No. :	MFCD00016810
Formula :	C₁₁H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RARLPRMZJNIQGU-UHFFFAOYSA-N
M.W :	186.21	Pubchem ID :	123485
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	54.84
TPSA :	55.12 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.82 cm/s

Log Po/w (iLOGP) :	1.49
Log Po/w (XLOGP3) :	2.28
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	2.16
Log Po/w (SILICOS-IT) :	1.3
Consensus Log Po/w :	1.74

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Safety of [ 39627-84-4 ]

Application In Synthesis of [ 39627-84-4 ]

[ 39627-84-4 ] Synthesis Path-Downstream 1~53

Related Functional Groups of
[ 39627-84-4 ]

Aryls

Amides

Hydrazides

Amines

Hydrazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.83
Solubility :	0.277 mg/ml ; 0.00149 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.157 mg/ml ; 0.000842 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.71
Solubility :	0.0359 mg/ml ; 0.000193 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.01

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P271-P302+P352-P305+P351+P338-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 39627-84-4 ] {[proInfo.proName]}

Quality Control of [ 39627-84-4 ]

Related Doc. of [ 39627-84-4 ]

Product Details of [ 39627-84-4 ]

Calculated chemistry of [ 39627-84-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 39627-84-4 ]

Application In Synthesis of [ 39627-84-4 ]

[ 39627-84-4 ] Synthesis Path-Downstream 1~53

Related Functional Groups of [ 39627-84-4 ]

Aryls

Amides

Hydrazides

Amines

Hydrazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 39627-84-4 ]