[ CAS No. 3332-29-4 ] {[proInfo.proName]}

Name: 3332-29-4|O-Ethylhydroxylamine hydrochloride|98%
Brand: Ambeed
SKU: A245975
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Quality Control of [ 3332-29-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 3332-29-4 ]

CAS No. :	3332-29-4	MDL No. :	MFCD00012956
Formula :	C₂H₈ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NUXCOKIYARRTDC-UHFFFAOYSA-N
M.W :	97.54	Pubchem ID :	76850
Synonyms :

Calculated chemistry of [ 3332-29-4 ]

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	22.49
TPSA :	35.25 Å²

Pharmacokinetics

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) :	-6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.5
Log Po/w (WLOGP) :	0.7
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	-0.73
Consensus Log Po/w :	0.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.69
Solubility :	19.7 mg/ml ; 0.202 mol/l
Class :	Very soluble
Log S (Ali) :	-0.81
Solubility :	15.1 mg/ml ; 0.155 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.12
Solubility :	128.0 mg/ml ; 1.31 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 3332-29-4 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	1325
Hazard Statements:	H315-H319-H228	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 3332-29-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3332-29-4 ]
Downstream synthetic route of [ 3332-29-4 ]

[ 3332-29-4 ] Synthesis Path-Upstream 1~3

1
[ 1914-21-2 ]
[ 3332-29-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With methylhydrazine In dichloromethane at 0 - 20℃; for 2 h; Stage #2: With hydrogenchloride In 1,4-dioxane at 0℃;	After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.27 ml of iodinated ethane (Aldrich) was added, and 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60° C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixture eluent of ethyl acetate/hexane (1:5) and then dried to obtain 518 mg of a compound (yield: 88percent). The compound was dissolved in 5 ml of dichloromethane, and 0.11 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 263 mg of a solid (yield: 100percent). 10 mg of the obtained solid and 44 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1013 (46 mg, yield: 96percent). ¹H-NMR (300 MHz, CDCl₃) δ5.91-5.76 (m, 2H), 5.34-5.32 (m, 1H), 5.28-5.25 (m, 1H), 5.14 (m, 1H), 4.24-4.10 (m, 3H), 4.04 (q, J=20.9 Hz, 2H), 3.64-3.48 (m, 1H), 2.42-0.60 (m, 38H)

Reference： [1] Patent: US2014/378399, 2014, A1, . Location in patent: Paragraph 0097
[2] Farmaco, Edizione Scientifica, 1987, vol. 42, # 10, p. 697 - 708
[3] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 184 - 194

2
[ 624-86-2 ]
[ 3332-29-4 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 26, p. 10857 - 10863

3
[ 22509-51-9 ]
[ 3332-29-4 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 4, p. 361 - 363

[ 3332-29-4 ] Synthesis Path-Downstream 1~39

1
[ 3332-29-4 ]
[ 153559-46-7 ]
cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid O-ethyloxime [ No CAS ]
4-[[(E)-Ethoxyimino]-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methyl]-benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 742 - 750

2
[ 3332-29-4 ]
[ 118-97-8 ]
N-ethoxy-4-carboxy-2,6-dinitrobenzenamine [ No CAS ]

Reference： [1]Revue Roumaine de Chimie,1999,vol. 44,p. 475 - 478

3
[ 1197-09-7 ]
[ 3332-29-4 ]
3,4-dihydroxyacetophenone-O-ethyloxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium acetate In water at 80℃; for 2h;

Reference： [1]Ley, Jakob P; Bertram, Heinz-Jürgen [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 7, p. 1879 - 1885]

4
[ 15174-69-3 ]
[ 3332-29-4 ]
4-hydroxy-3-methylbenzaldehyde-O-ethyloxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium acetate In water at 80℃; for 2h;

Reference： [1]Ley, Jakob P; Bertram, Heinz-Jürgen [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 7, p. 1879 - 1885]

5
[ 3332-29-4 ]
[ 160296-40-2 ]
[ 438208-38-9 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3143 - 3160

6
[ 1009-11-6 ]
[ 3332-29-4 ]
1-(4-hydroxy-phenyl)-butan-1-one <i>O</i>-ethyl-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5051 - 5056

7
[ 3332-29-4 ]
[ 70-70-2 ]
(E)-1-(4-hydroxyphenyl)propan-1-one-O-ethylketoxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium acetate In ethanol at 80℃; for 4h;	54.54A Embodiment 54A (E)-1-(4-hydroxyphenyl)-propan-1-one-O-ethyl ketoxime Agitate the mixture solution of 4-hydroxyphenyl acetone (1 g, 6.7 mmol), sodium acetate (1.1 g, 3.3 mmol), ethoxyamine hydrochloride (814 mg, 13.3 mmol) in ethanol (10 ml) 2 hours at 80° C. Then add water (10 ml) and ethyl acetate (20 ml) into the reaction system. Then extract the aqueous layer with ethyl acetate (20 ml×3) before filter and evaporate to obtain the title compound (brown solid, 1.28 g, yield of 99%). 1H NMR(400 MHz,CDCl3)7.48(d,J=8.5 Hz,2H),6.74-6.79(m,2H),4.20(q,J=7.0 Hz,2H),2.72(q,J=7.7 Hz,2H),1.30(t,J=7.0 Hz,3H),1.11(t,J=7.5 Hz,3H).
	With sodium acetate at 80℃; for 2h;

Reference： [1]Current Patent Assignee: JIANGSU KANION PHARMACEUTICAL CO., LTD. - US2017/66732, 2017, A1 Location in patent: Paragraph 0457-0458
[2]Chern, Jyh-Haur; Lee, Chung-Chi; Chang, Chih-Shiang; Lee, Yen-Chun; Tai, Chia-Liang; Lin, Ying-Ting; Shia, Kak-Shan; Lee, Ching-Yin; Shih, Shin-Ru [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 20, p. 5051 - 5056]

8
[ 776-99-8 ]
[ 3332-29-4 ]
N-(1-methyl-2-(3,4-dimethoxy-phenyl)-ethyl)-O-ethyl-hydroxylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1-(3,4-Dimethoxyphenyl)-2-propanone (1.35 g, 7.5 mmol) was dissolved in H2O (15 ml) and a solution of O-ethylhydroxylamine hydrochloride (1 g, 10 mmol) and Na2CO3 (0.53 g, 5 mmol) in water (10 ml) was added dropwise under stirring at 10C. The reaction was left at room temperature overnight and then extracted with diethyl ether. After evaporation of the solvent, the residue was dissolved in EtOH (20 ml) and concentrated hydrochloric acid (1 ml), then hydrogenated over PtO2 at 3,6 x 106 Pa (50 psi). The solvent was removed under vacuum. The residue was dissolved in 30 ml of water, the aqueous phase was made basic with NaHCO3 and extracted with ethyl acetate The organic phase was dried over MgSO4, filtered and concentrated to dryness. The crude residue was purified by flash chromatography, to afford 0.75 g of the title compound. MS (EI): 239.3 (M+).Example 5

Reference： [1]Patent: EP1541547,2005,A1 .Location in patent: Page/Page column 9

9
[ 885588-03-4 ]
[ 3332-29-4 ]
3-[(4-iodo-2-fluorophenyl)amino]-N-ethoxyisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Step 2: 3-[(4-lodo-2-fluoro)amino]isonicotinic acid from step 1 (200mg, 0.559mmol) was dissolved in 4ml dry DMF followed by the addition of DIPEA (0.671 mmol, 121 mul), PyBOP (0.371 mmol, 350mg) and O-ethylhydroxylamine hydrochloride (1.12mmol, 110mg). The mixture was stirred at ambient temperature over night and the volatiles were removed in vacuo. The crude material was purified by preparative RP-HPLC to give 113mg (282mmol; 50% yield) of the pure title compound] . LC-MS (method III): rt = 7.03min; m/z [M+H]+ 402.

Reference： [1]Patent: WO2006/45514,2006,A1 .Location in patent: Page/Page column 79

10
[ 3332-29-4 ]
[ 4490-82-8 ]
[ 64606-80-0 ]
1-butoxy-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Similarly, 1-ethoxy-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea and 1-butoxy-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea are prepared by using ethoxyamine hydrochloride and n-<strong>[4490-82-8]butoxyamine hydrochloride</strong>, respectively, in place of methoxyamine hydrochloride.

Reference： [1]Patent: US4036979,1977,A

11
[ 32066-29-8 ]
[ 3332-29-4 ]
[ 1032392-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 65℃; for 2h;	1.A A mixture of methyl 3-(4-hydroxyphenyl)-3-oxopropanoate (1 g) and EtONH2.HCl (600 mg) in methanol (10 mL) was heated at 65° C. for 2 h. Methanol was removed in vacuo, and saturated sodium bicarbonate was added to the residue. The aqueous solution was extracted with ethyl acetate (×4), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound as a colorless oil, which was used directly in Step B. HPLC retention time: 1.51 min (method A). MS (ESI) (M+H)+ 238.09.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/139523, 2008, A1 Location in patent: Page/Page column 7; 8

12
[ 193274-53-2 ]
[ 3332-29-4 ]
[ 1188338-00-2 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With triethylamine In ethanol; water at 55 - 60℃; for 1.75h;

Reference： [1]Location in patent: experimental part Chai, Yun; Wan, Zhi-Long; Wang, Bo; Guo, Hui-Yuan; Liu, Ming-Liang [European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4063 - 4069]

13
[ 3332-29-4 ]
[ 175463-32-8 ]
[ 1257127-35-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 5498 - 5506

14
[ 3332-29-4 ]
[ 175463-32-8 ]
[ 1339961-05-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; In methanol; at 20℃;	General procedure: To a solution of methoxylamine/ethoxylamine hydrochloride (1.2 mol) and pyridine (80 mL, 1.0 mol) dissolved in MeOH (1000 mL) was added N-tert-butoxycarbonyl-3-cyano-4-oxopyrrolidine (5, 210 g, 1.0 mol) at room temperature. The reaction mixture was stirred at the same temperature overnight and concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the title compounds 6a,b as light yellow oils. The crude products were used directly without further purification.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8264 - 8270

15
[ 145-13-1 ]
[ 3332-29-4 ]
(E)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone O-ethyl oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine at 95℃; for 0.3h; Inert atmosphere;
97%	With pyridine at 95℃; for 18h; Inert atmosphere;	1 (E)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone O-ethyl oxime (S11) (E)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone O-ethyl oxime (S11) A round bottom flask was charged with 5-pregnen-3β-ol-20-one (3.16 g, 10.0 mmol), O-ethylhydroxylamine hydrochloride (1.07 g, 11.0 mmol), and pyridine (10 mL) under nitrogen. The stirred mixture was heated at 95° C. for 18 h, cooled to room temperature, poured into water (100 mL), and stirred for 15 min. The white solid was collected by filtration, washed with water, and dried in vacuo. The solid was purified by flash chromatography (9:1 DCM:EtOAc) to afford S11 (3.49 g, 97% yield) as a white solid, mp 119-121° C.; 1H NMR (400 MHz, CDCl3) δ: 5.38-5.29 (m, 1H), 4.05 (q, J=7.0 Hz, 2H), 3.55-3.47 (m, 1H), 2.33-2.07 (m, 4H), 1.99 (well resolved doublet of multiplets centered at 1.99 ppm, J=17.3 Hz, 1H), 1.91-1.76 (m, 2H), 1.80 (s, 3H), 1.72-1.36 (m, 10H), 1.33-1.13 (m, 1H), 1.22 (t, J=7.0 Hz, 3H), 1.13-1.01 (m, 2H), 1.01-0.90 (m, 1H), 0.99 (s, 3H), 0.62 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 157.1, 140.7, 121.4, 71.6, 68.6, 56.6, 56.1, 50.1, 43.6, 42.1, 38.6, 37.2, 36.5, 32.0, 31.7, 31.5, 24.2, 23.0, 21.0, 19.4, 15.7, 14.7, 13.1. Analysis calcd for C23H37NO2: C, 76.83; H, 10.37; N, 3.90. Found: C, 76.63; H, 10.19; N, 3.88. HRMS-ESI calcd for C23H38NO2 [M+H]+: 360.29025. found: 360.29025.
97%	With pyridine at 95℃; for 18h; Inert atmosphere;	1 (E)-l-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl- 2,3,4,7,8,9, 10, 11 , 12, 13, 14, 15, 16, 17-tetradecahydro- 1 H-cyclopenta[a]phenanthren- 17-yl)ethanone O- ethyl oxime (SI 1). A round bottom flask was charged with 5-pregnen-3 -ol-20-one (3.16 g, 10.0 mmol), O- ethylhydroxylamine hydochloride (1.07 g, 11.0 mmol), and pyridine (10 mL) under nitrogen. The stirred mixture was heated at 95°C for 18 h, cooled to room temperature, poured into water (100 mL), and stirred for 15 min. The white solid was collected by filtration, washed with water, and dried in vacuo. The solid was purified by flash chromatography (9: 1 DCM:EtOAc) to afford SI 1 (3.49 g, 97%> yield) as a white solid.

Reference： [1]Guthrie, David B.; Stein, Donald G.; Liotta, Dennis C.; Lockwood, Mark A.; Sayeed, Iqbal; Atif, Fahim; Arrendale, Richard F.; Reddy, G. Prabhakar; Evers, Taylor J.; Marengo, Jose R.; Howard, Randy B.; Culver, Deborah G.; Natchus, Michael G. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 362 - 366]
[2]Current Patent Assignee: EMORY UNIVERSITY - US2013/210785, 2013, A1 Location in patent: Paragraph 0280-0281
[3]Current Patent Assignee: EMORY UNIVERSITY - WO2015/23593, 2015, A1 Location in patent: Paragraph 00378; 00379

16
[ 3332-29-4 ]
[ 231958-04-6 ]
[ 1621384-38-0 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: To a stirred solution of compound 7 (5.0 g, 19.9 mmol) in DMF (30 mL) was added EDC (3.9 mL, 21.9 mmol), HOBt (3.35 g, 21.9 mmol). After stirring at rt for 30 min, methoxyamine hydrochloride (1.83 g, 21.9 mmol) was added. The resulting mixture was stirred for another 10 min, and cooled to 0 C. DIPEA (8.09 mL, 46.4 mmol) was added slowly to maintain the internal reaction temperature below 25 C. After finishing the addition, the reaction mixture was allowed to warm to rt and stirred at rt overnight. The resulting mixture was poured into water and extracted with EtOAc. The combined organic layer was washed with cold 0.5 N HCl and water. The organic layer was then extracted with cold 0.5 N NaOH, and the combined basic aqueous extract was adjusted pH to 8 by a slow addition of cold 0.5 N HCl. The resulting precipitate was collected by filtration, and washed with cold water. The crude product was recrystallized in EtOH to afford 8a (5.17 g, 98 %) as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3700 - 3705

17
[ 3332-29-4 ]
[ 23611-75-8 ]
6-chloro-N-ethoxypyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With trimethylaluminum; In hexane; dichloromethane; at 20℃;Inert atmosphere;	1.78 g (10.31 mmol) of <strong>[23611-75-8]methyl <strong>[23611-75-8]6-chloropyrazine-2-carboxylate</strong></strong> synthesized by the method described in Non Patent Literature 1 was dissolved in 20 ml of methylene chloride. To this solution, 1.47 g (17.60 mmol) of O-ethylhydroxylammonium chloride was added. Thereafter, 21.5 ml (1.0 M, n-hexane solution, 21.5 mmol) of trimethylaluminum was added dropwise under nitrogen atmosphere and ice cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and Celite filtration was carried out. Then it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the inorganic matter was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.08 g (10.31 mmol, yield 100%) of 6-chloro-N-ethoxypyrazine-2-carboxamide.

Reference： [1]Patent: JP2016/30742,2016,A .Location in patent: Paragraph 0155-0157

18
[ 3332-29-4 ]
[ 6299-87-2 ]
6-chloro-N-ethoxypyridine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		<strong>[6299-87-2]6-hydroxypyrimidine-4-carboxylic acid</strong> 1.00 g (7.14 mmol),30 ml of methylene chloride, 3.60 g (28.4 mmol) of oxalyl chloride and 0.05 g (0.68 mmol) of N, N-dimethylformamide were added to 1.00 g (7.14 mmol), and the mixture was heated under reflux for 3 hours. Then, the reaction solution was concentrated under reduced pressure. To the obtained residue was added 30 ml of methylene chloride, 0.70 g (7.18 mmol) of O-ethylhydroxylammonium chloride and 1.45 g (14.3 mmol) of triethylamine were added under ice cooling, and the mixture was stirred at room temperature for 3 hours . Then, the reaction solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography Further purification gave 0.79 g (3.92 mmol, yield 55percent) of 6-chloro-N-ethoxypyridine-4-carboxamide.

Reference： [1]Patent: JP2016/30742,2016,A .Location in patent: Paragraph 0168-0170

19
[ 66389-80-8 ]
[ 3332-29-4 ]
tert-butyl N({4-[N’-ethoxy-carbamimidoyl]phenyl}methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.0 g	With mercaptoacetic acid; triethylamine; In ethanol; at 90℃; for 24h;	Step 1: Tert-butyl N-[(4-cyanophenyl)methyljcarbamate (2.00 g; 8.61 mmol) wassuspended in ethanol (14.00 ml). Triethylamine (4.20 ml; 30.14 mmol) and a 30% W/Wsolution of O-ethylhydroxylamine hydrochloride (1.68 g; 17.22 mmol) were added to the mix, followed by the addition of thioglycolic acid (0.60 ml; 8.61 mmol). The resulting mixture was stirred for 24 h at 90 C. The solvent was removed under vacuum and the residue was partitioned in EtOAc/water. The organic layer was isolated and the aqueous phaseextracted 2 times; the combined organics were washed with brine, filtered and concentrated. The crude was purified by flash chromatography (Heptane/EtOAc = 3:1) to give tert-butyl N({4- [N?-ethoxy-carbamimidoyl jphenyl } methyl)carbamate (1.0 g).

Reference： [1]Patent: WO2016/201052,2016,A1 .Location in patent: Page/Page column 285

20
[ 31191-08-9 ]
[ 3332-29-4 ]
(E)-5-hydroxypyridinecarboxaldehyde-O-ethylketoxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium acetate; In water; at 80℃; for 2h;	Heat the aqueous solution (5 ml) of ethoxyamino hydrochloride (244 mg, 2.5 mmol), 5-hydroxy-pyridine-2-aldehyde (308 mg, 2.5 mmol), sodium acetate (410 mg, 5.0 mmol) to 80° C. to agitate 2 hours. After TLC indicates the raw materials disappear, extract the reaction mixture with ethyl acetate (10 ml×3). Mix the organic phases and dry with anhydrous Na2SO4 before filter and concentrate to obtain the title compound (white solid, 410 mg, yield of 99percent) that is directly used without necessity to purify further.

Reference： [1]Patent: US2017/66732,2017,A1 .Location in patent: Paragraph 0471-0472

21
[ 3470-50-6 ]
[ 3332-29-4 ]
(E)-6-hydroxy-3,4-dihydronaphthalene-1(2H)-one-O-ethylketoxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium acetate; In water; at 80℃; for 2h;	Add ethoxyamino hydrochloride (1.88 g, 30.9 mmol) and sodium acetate (2.5 g, 30.9 mmol) into the solution of 6-hydroxy-1-tetralone (1 g, 6.2 mmol) in water (10 ml). Agitate the mixture solution 2 hours at 80 C. Then extract it with ethyl acetate. Dry the organic phase with anhydrous Na2SO4 before filter and evaporate to obtain the title compound (yellow solid, 0.8 g, yield of 63%). LCMS(ESI)m/z:206(M+1).

Reference： [1]Patent: US2017/66732,2017,A1 .Location in patent: Paragraph 0536-0537

22
[ 3332-29-4 ]
[ 21900-42-5 ]
N-ethoxy-2,4-dimethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
840 mg	With potassium carbonate In water; ethyl acetate at 0℃; for 4h;
	With potassium carbonate In water; ethyl acetate at 0℃; for 4h;

Reference： [1]Wu, Xiaowei; Wang, Bao; Zhou, Yu; Liu, Hong [Organic Letters, 2017, vol. 19, # 6, p. 1294 - 1297]
[2]Nasier, Abudulajiang; Chang, Xihao; Guo, Chang [Journal of Organic Chemistry, 2021, vol. 86, # 22, p. 16068 - 16076]

23
[ 1029439-49-3 ]
[ 3332-29-4 ]
O-ethyl-N-(3-fluoro-4-(44,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)hydroxylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With N-ethyl-N,N-diisopropylamine; at 60℃; for 12h;Inert atmosphere;	To a solution of 2-(4-(bromomethyl)-2-fluorophenyl)-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane (2.5 g, 7.94 mmol) in N,N-dimethylformamide (12.41 ml) was added DIPEA (3.47 ml, 19.84 mmol), O-ethylhydroxylamine hydrochloride (1 .548 g, 15.87 mmol) and the reaction mixture was heated to 60 C for 12 hr. The mixture was diluted with EtOAc (50 mL) and water (100 ml) and the mixture was extracted with EtOAc (30 ml x 3) and the combined organic layers were washed with brine (30 mL), dried over sodium sulphate and concentrated to give 0-ethyl-N-(3-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)benzyl)hydroxylamine (2.4 g, 3.58 mmol, 45 % yield). LCMS: [M+H] 295.1.

Reference： [1]Patent: WO2017/98440,2017,A1 .Location in patent: Page/Page column 197

24
[ 3332-29-4 ]
[ 2251-65-2 ]
N-ethoxy-3-trifluoromethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.2%	With potassium carbonate In dichloromethane; water at -10 - -5℃; for 6h;	7.1 To a 250 mL four-necked flask was added 100 ml of water,N-ethoxyamine hydrochloride 10.60 g (0.11 mol)Down to -5 ° C, slowly add potassium carbonate saturated solution, adjust the solution pH to 8-8.5,Continue to cool down to -10 ° C, 3-Trifluoromethylbenzoyl chloride 20.70 g (0.10 mol)Of methylene chloride solution was stirred at -10 ° C for 6 h. Back to room temperature,With dilute hydrochloric acid to adjust the pH to neutral solution, divided into the water layer,The organic layer was washed with water (150 mL x 3), the organic layer was collected,N-ethoxy-3-trifluoromethylbenzamide IV (b) was distilled under reduced pressure in a yield of 93.2%

Reference： [1]Current Patent Assignee: JIANGSU KUAIDA AGROCHEMICAL - CN106883110, 2017, A Location in patent: Paragraph 0015

25
[ 3332-29-4 ]
[ 480-41-1 ]
(E)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one O-ethyl oxime [ No CAS ]

Reference： [1]International Journal of Molecular Sciences,2019,vol. 20

26
[ 68742-28-9 ]
[ 3332-29-4 ]
[ 530-62-1 ]
N-ethoxy-5-ethyl-1H-indole-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: O-ethylhydroxylamine hydrochloride With sodium hydroxide In tetrahydrofuran at 20℃; for 3h; Stage #2: 5-ethyl-1H-indole; 1,1'-carbonyldiimidazole With dmap In tetrahydrofuran; acetonitrile at 85℃; for 10h; Inert atmosphere; Stage #3: O-ethylhydroxylamine hydrochloride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere;

Reference： [1]Yang, Lisheng; Li, Chunpu; Wang, Dechuan; Liu, Hong [Journal of Organic Chemistry, 2019, vol. 84, # 11, p. 7320 - 7330]

27
[ 10501-17-4 ]
[ 3332-29-4 ]
[ 530-62-1 ]
N,5-diethoxy-1H-indole-1-carboxamide [ No CAS ]