Name: 28657-75-2|1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone|98%
Brand: Ambeed
SKU: A808183
Rating: 95 (26 reviews)

1
[ 56136-84-6 ]
[ 28657-75-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 12h;	1.1 Dissolve 6-nitro-3,4-methylenedioxyacetophenone (7.8g, 37.3mmol) in ethyl acetate (70ml), add a catalytic amount of palladium on carbon, fill with hydrogen balloon, stir the reaction at room temperature for 12h , Filter to remove the catalyst,After concentration, 5.5 g of 6-amino-3,4-methylenedioxyacetophenone was obtained as a pale yellow solid.The yield was 83%.
83%	With palladium on activated charcoal; hydrogen In ethyl acetate for 12h;	1 6-nitro-3,4-methylenedioxyacetophenone(7.8g, 37.3mmol) was dissolved in ethyl acetate(70mL) and catalytic amount Pd/C was added. The mixture reacted under hydrogen balloon for 12hr. The catalyst was filtered out and the filtrate was concentrated. The resultant was 5.5g light yellow solid (83%). mp 123-124 °C.
81%	With hydrogen In ethanol

67%	With hydrogen In ethanol Ambient temperature;
	With hydrogen In ethanol Ambient temperature;
	With hydrogen In methanol

Reference： [1]Current Patent Assignee: MARINE BIOMEDICAL RES INST QINGDAO - CN110590796, 2019, A Location in patent: Paragraph 0073-0075; 0077
[2]Current Patent Assignee: CANGET BIOTEKPHARMA; ZHEJIANG UNIVERSITY OF TECHNOLOGY - WO2020/61106, 2020, A2 Location in patent: Paragraph 000118; 000120
[3]Bertha, P.; Fetter, J.; Lempert, K.; Moeller, J.; Radics, L. [Journal of Chemical Research, Miniprint, 1980, # 12, p. 4737 - 4744]
[4]Barta-Szalai, G.; Fetter, J.; Lempert, K.; Moller, J. [Acta Chimica Academiae Scientiarum Hungaricae, 1980, vol. 104, p. 253 - 266]
[5]Phillips; Castle [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 7, p. 1489 - 1495]
[6]Bandurco, Victor T.; Schwender, Charles F.; Bell, Stanley C.; Combs, Donald W.; Kanojia, Ramesh M.; et al. [Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1421 - 1426]

2
[ 1711-05-3 ]
[ 28657-75-2 ]
N-(6-Acetyl-benzo[1,3]dioxol-5-yl)-3-methoxy-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 0 - 20℃;
	With triethylamine In dichloromethane at 20℃; Cooling with ice;

Reference： [1]Li; Wang; Kuo; Wu; Lednicer; Lin; Hamel; Lee - [Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1126 - 1135]
[2]Yang, Rui; Li, Zhuolin; Xie, Jialing; Liu, Jianchuan; Qin, Tianhong; Liu, Junda; Du, Haiying; Ye, Haoyun [Chemistry and biodiversity, 2021, vol. 18, # 5]

3
[ 28657-75-2 ]
[ 98-88-4 ]
[ 903297-11-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine In tetrahydrofuran at 0 - 20℃;
	With triethylamine In dichloromethane at 0℃;

With triethylamine In dichloromethane at 20℃; Cooling with ice;

Reference： [1]Verma, Ajay; Kumar, Sangit [Organic Letters, 2016, vol. 18, # 17, p. 4388 - 4391]
[2]Li; Wang; Kuo; Wu; Lednicer; Lin; Hamel; Lee - [Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1126 - 1135]
[3]Zhao, Dan; Wang, Teng; Shen, Qi; Li, Jian-Xin [Chemical Communications, 2014, vol. 50, # 33, p. 4302 - 4304]
[4]Yang, Rui; Li, Zhuolin; Xie, Jialing; Liu, Jianchuan; Qin, Tianhong; Liu, Junda; Du, Haiying; Ye, Haoyun [Chemistry and biodiversity, 2021, vol. 18, # 5]

4
[ 28657-75-2 ]
[ 393-52-2 ]
[ 666818-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 0 - 20℃;
	With triethylamine In tetrahydrofuran at 0 - 20℃;
	With triethylamine In dichloromethane at 20℃; Cooling with ice;

Reference： [1]Li; Wang; Kuo; Wu; Lednicer; Lin; Hamel; Lee - [Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1126 - 1135]
[2]Xia; Yang; Xia; Hackl; Hamel; Mauger; Wu; Lee [Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3932 - 3936]
[3]Yang, Rui; Li, Zhuolin; Xie, Jialing; Liu, Jianchuan; Qin, Tianhong; Liu, Junda; Du, Haiying; Ye, Haoyun [Chemistry and biodiversity, 2021, vol. 18, # 5]

5
[ 28657-75-2 ]
[ 1711-07-5 ]
N-(6-Acetyl-benzo[1,3]dioxol-5-yl)-3-fluoro-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 0 - 20℃; for 2.5h;
	With triethylamine In dichloromethane at 20℃; Cooling with ice;

Reference： [1]Li, Leping; Wang, Hui-Kang; Kuo, Sheng-Chu; Wu, Tian-Shung; Mauger, Anthony; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3400 - 3407]
[2]Yang, Rui; Li, Zhuolin; Xie, Jialing; Liu, Jianchuan; Qin, Tianhong; Liu, Junda; Du, Haiying; Ye, Haoyun [Chemistry and biodiversity, 2021, vol. 18, # 5]

6
[ 28657-75-2 ]
[ 121-90-4 ]
[ 178983-58-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In tetrahydrofuran at 0 - 20℃; for 2.5h;

Reference： [1]Li, Leping; Wang, Hui-Kang; Kuo, Sheng-Chu; Wu, Tian-Shung; Mauger, Anthony; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3400 - 3407]

7
[ 28657-75-2 ]
[ 591-31-1 ]
[ 204841-35-0 ]

Yield	Reaction Conditions	Operation in experiment
54.5%	With sodium hydroxide In ethanol for 24h; Ambient temperature;
	With sodium hydroxide

Reference： [1]Xia, Yi; Yang, Zheng-Yu; Xia, Peng; Bastow, Kenneth F.; Tachibana, Yoko; Kuo, Sheng-Chu; Hamel, Ernest; Hackl, Torben; Lee, Kuo-Hsiung [Journal of Medicinal Chemistry, 1998, vol. 41, # 7, p. 1155 - 1162]
[2]Xia, Yi; Yang, Zheng-Yu; Xia, Peng; Bastow, Kenneth F.; Nakanishi, Yuka; Lee, Kuo-Hsiung [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 8, p. 699 - 701]

8
[ 28657-75-2 ]
[ 244245-71-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 2-amino-4,5-methylenedioxy-acetophenone With acetic acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide for 5h;
83%	Stage #1: 2-amino-4,5-methylenedioxy-acetophenone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 1.5h;
	Stage #1: 2-amino-4,5-methylenedioxy-acetophenone With boron trifluoride diethyl etherate; isopentyl nitrite In tetrahydrofuran; dichloromethane at -15 - 5℃; Stage #2: With pyridine; benzylaminomethyl polystyrene In dichloromethane; acetonitrile at -15 - 25℃; Stage #3: With trimethylsilylazide; trifluoroacetic acid In dichloromethane at 20℃; for 0.0833333h;

With sodium azide; acetic acid; sodium nitrite In water at 0 - 20℃; for 2h;

Reference： [1]Guggenheim, Kathryn G.; Toru, Hannah; Kurth, Mark J. [Organic Letters, 2012, vol. 14, # 14, p. 3732 - 3735]
[2]Molina; Tarraga; Lopez; Martinez [Journal of Organometallic Chemistry, 1999, vol. 584, # 1, p. 147 - 158]
[3]Avemaria, Frank; Zimmermann, Viktor; Bräse, Stefan [Synlett, 2004, # 7, p. 1163 - 1166]
[4]Wu, Xiang; Zheng, Lang-Lang; Zhao, Li-Ping; Zhu, Cheng-Feng; Li, You-Gui [Chemical Communications, 2019, vol. 55, # 98, p. 14769 - 14772]

9
[ 86-81-7 ]
[ 28657-75-2 ]
[ 421766-44-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide In ethanol at 59.85 - 69.85℃; for 0.25h;
	With sodium hydroxide In ethanol; water Reflux;

Reference： [1]Low, John N.; Cobo, Justo; Nogueras, Manuel; Sanchez, Adolfo; Albornoz, Andrea; Abonia, Rodrigo [Acta Crystallographica, Section C: Crystal Structure Communications, 2002, vol. 58, # 1, p. o42-o45]
[2]Location in patent: scheme or table Abonia, Rodrigo; Cuervo, Paola; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo [European Journal of Organic Chemistry, 2008, # 27, p. 4684 - 4689]

10
[ 24424-99-5 ]
[ 28657-75-2 ]
(6-acetyl-benzo[1,3]dioxol-5-yl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: di-<i>tert</i>-butyl dicarbonate; 2-amino-4,5-methylenedioxy-acetophenone With polymer supported DMAP In dichloromethane at 25℃; for 1.5h; Stage #2: In dichloromethane at 25℃; for 1h;

Reference： [1]Broutin, Pierre-Emmanuel; Hilty, Peter; Thomas, Andrew W. [Tetrahedron Letters, 2003, vol. 44, # 34, p. 6429 - 6432]

11
[ 24424-99-5 ]
[ 28657-75-2 ]
8-methylene-6-oxo-8H-1,3,7-trioxa-5-aza-cyclopenta[b]naphthalene-5-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap In dichloromethane at 25℃; for 0.5h;

Reference： [1]Broutin, Pierre-Emmanuel; Hilty, Peter; Thomas, Andrew W. [Tetrahedron Letters, 2003, vol. 44, # 34, p. 6429 - 6432]

12
[ 28657-75-2 ]
6,7-methylenedioxy-4-cinnolone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 2-amino-4,5-methylenedioxy-acetophenone With hydrogenchloride; sodium nitrite In water at -5℃; for 1h; Stage #2: In water Heating;

Reference： [1]Ruchelman, Alexander L.; Singh, Sudhir K.; Ray, Abhijit; Wu, Xiaohua; Yang, Jin-Ming; Zhou, Nai; Liu, Angela; Liu, Leroy F.; LaVoie, Edmond J. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 4, p. 795 - 806]

13
[ 28657-75-2 ]
[ 109-94-4 ]
[ 35478-79-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogenchloride; sodium methylate In 1,2-dimethoxyethane; water	3 Process for Producing 6,7-Methylenedioxy-4-Quinolone Example 3 Process for Producing 6,7-Methylenedioxy-4-Quinolone 6-Amino-3,4-(methylenedioxy)-acetophenone (5.0 g, 28 mmol) was added to and dissolved in dimethoxyethane (150 ml). To the solution obtained was added sodium methoxide (4.5 g, 84 mmol), and the mixture was stirred at room temperature for 30 minutes. Ethyl formate (12 ml, 143 mmol) was then added, and the mixture was stirred at room temperature for an additional 160 minutes. After adding water (5 ml) to the reaction solution, and stirring for 10 minutes, 10% hydrochloric acid was added to the mixture for neutralization, thereby causing precipitation. The precipitate was collected by filtration, and washed with water (25 ml*2). The product obtained was dried at 40° C. under reduced pressure to give 4.9 g of the desired product (yield 94%). 1H-NMR (DMSO-d6, 500 MHz): δ 5.93 (d, J=7.3 Hz, 1H), 6.12 (s, 2H), 6.97 (s, 1H), 7.38 (s, 1H), 7.75 (d, J=7.3 Hz, 1H), 11.59 (s, 1H). Mass Spectrometry (FD-MS, m/z): 189 (M+).
89%	With sodium hydride Heating;

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - US6187926, 2001, B1
[2]Ruchelman, Alexander L.; Houghton, Peter J.; Zhou, Nai; Liu, Angela; Liu, Leroy F.; LaVoie, Edmond J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 792 - 804]

14
[ 28657-75-2 ]
[ 100-51-6 ]
1-(6-aminobenzo[d][1,3]dioxol-5-yl)-3-phenylpropan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hydroxide In 1,4-dioxane at 80℃; for 24h;
54%	With dichlorotetrakis(dimethyl sulfoxide)ruthenium(II); potassium hydroxide In 1,4-dioxane at 80℃; for 24h;

Reference： [1]Martínez, Ricardo; Ramón, Diego J.; Yus, Miguel [Tetrahedron, 2006, vol. 62, # 38, p. 8988 - 9001]
[2]Kim, Young Min; Yoo, Hyung-Seok; Son, Seung Hwan; Kim, Ga Yeong; Jang, Hyu Jeong; Kim, Dong Hwan; Kim, Soo Dong; Park, Boyoung Y.; Kim, Nam-Jung [European Journal of Organic Chemistry, 2021, vol. 2021, # 4, p. 618 - 622]

15
[ 28657-75-2 ]
[ 98-59-9 ]
[ 460994-52-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine In dichloromethane at 20℃;
84%	With pyridine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	General Procedure A: Sulfonylation of amino-ketones. General procedure: To a solution of 2'-aminoacetophenone (1 equiv), pyridine (1.3 equiv) in CH2Cl2 (0.5 mol/L) was added TsCl (1.05 equiv) at 0 °C. The mixture was gradually warmed to room temperature and stirred for 12 h. The resulting reaction mixture was concentrated to one-third volume. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed successively with 1 mol/L HCl, H2O, and sat. aqueous NaCl, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by recrystallization or chromatographic purification of the crude product to give keto-sulfonamides 1a-f-1 and 1h-1.
	With pyridine at 20℃; Inert atmosphere;

	With pyridine at 20℃; for 4h; Inert atmosphere;
	With pyridine at 20℃; for 4h; Inert atmosphere;

Reference： [1]Hari, Yoshiyuki; Kanie, Tomoki; Miyagi, Takashi; Aoyama, Toyohiko [Synthesis, 2006, # 8, p. 1249 - 1252]
[2]Noji, Masahiro; Kadowaki, Hiroto; Kubota, Yuuki; Yoshida, Tomomi; Saito, Noriko; Yamaguchi, Subaru; Ohata, Ren; Ishii, Keitaro; Takanami, Toshikatsu [Heterocycles, 2017, vol. 95, # 2, p. 1041 - 1073]
[3]Kothandaraman, Prasath; Huang, Chuhui; Susanti, Dewi; Rao, Weidong; Chan, Philip Wai Hong [Chemistry - A European Journal, 2011, vol. 17, # 36, p. 10081 - 10088]
[4]Location in patent: experimental part Kothandaraman, Prasath; Mothe, Srinivasa Reddy; Toh, Sharon Si Min; Chan, Philip Wai Hong [Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7633 - 7640]
[5]Kothandaraman, Prasath; Koh, Bing Qin; Limpanuparb, Taweetham; Hirao, Hajime; Chan, Philip Wai Hong [Chemistry - A European Journal, 2013, vol. 19, # 6, p. 1978 - 1985]

16
[ 872-85-5 ]
[ 28657-75-2 ]
[ 945868-98-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide In ethanol at 20℃; for 3h;

Reference： [1]Cuervo, Paola; Abonia, Rodrigo; Cobo, Justo; Low, John N.; Glidewell, Christopher [Acta Crystallographica, Section C: Crystal Structure Communications, 2007, vol. 63, # 2, p. o99-o101]

17
[ 350-03-8 ]
[ 28657-75-2 ]
8-methyl-6-(pyridin-3-yl)-[1,3]dioxolo[4,5-g]quinoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With (Bu₄N)₂S₂O₈ In neat (no solvent) at 20℃; for 1h;	Ethyl-2-methyl-4-phenylquinoline-3-carboxylate (3a) (typical procedure) General procedure: A mixture of o-aminobenzophenone (1.97 g, 10 mmol), ethyl acetoacetate (1.30 g, 10 mmol), and (Bu4N)2S2O8, (0.108 g, 25 mol%) was stirred at ambient temperature under solvent-free conditions for the appropriate time (Table 1) until starting material could no longer be detected by TLC (petroleum ether/EtOAc, 9:1). After completion of the reaction, the mixture was diluted with ethyl acetate (30 mL), washed with water (15 mL), dried (Na2SO4), and concentrated. The residue was purified by silica-gel column chromatography (10% ethyl acetate in hexane) to afford the pure product 3a as a pale yellow solid (2.76 g, 95%).
81%	With chloro-trimethyl-silane In N,N-dimethyl-formamide at 95℃;

Reference： [1]Vanajatha; Prabhakar Reddy [Synthetic Communications, 2016, vol. 46, # 23, p. 1953 - 1961]
[2]Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Plaskon, Andrey S.; Naumchik, Vasiliy S.; Tolmachev, Andrei A. [Synthesis, 2007, # 8, p. 1214 - 1224]

18
[ 28657-75-2 ]
[ 830-13-7 ]
C₂₁H₂₇NO₂*HCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With chloro-trimethyl-silane In N,N-dimethyl-formamide at 95℃;

Reference： [1]Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Plaskon, Andrey S.; Naumchik, Vasiliy S.; Tolmachev, Andrei A. [Synthesis, 2007, # 8, p. 1214 - 1224]

19
[ 28657-75-2 ]
1-(6-aminobenzo[d][1,3]dioxol-5-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium tetrahydroborate In ethanol for 1.5h; Heating;

Reference： [1]Martínez-Viturro, Carlos M.; Domínguez, Domingo [Tetrahedron Letters, 2007, vol. 48, # 6, p. 1023 - 1026]

20
[ 28657-75-2 ]
12-(2-amino-ethyl)-2,3-dimethoxy-12H-8,10-dioxa-6,12-diaza-cyclopenta[b]chrysen-13-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 89 percent / NaH / Heating 2.1: 91 percent / POCl₃ / 2 h / Heating 3.1: phenol / 2.5 h / Heating 3.2: 75 percent / phenol / 20 h / Heating 4.1: 1.70 g / Et₃N / CH₂Cl₂ / 16 h / Heating 5.1: 63 percent / Pd(OAc)2; P(o-tolyl)3; Ag₂CO₃ / dimethylformamide / 0.5 h / Heating 6.1: 80 percent / formic acid; AcOH / Pd black / 1.5 h / 20 °C