57508-48-2|Ethyl 2-Amidinoacetate Hydrochloride| Ambeed

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Quality Control of [ 57508-48-2 ] Purity: 97% SDS Specification

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Product Details of [ 57508-48-2 ]

CAS No. :	57508-48-2
Formula :	C₅H₁₁ClN₂O₂
M.W :	166.61
SMILES Code :	O=C(OCC)CC(N)=N.[H]Cl
MDL No. :	MFCD06797615
InChI Key :	VOHFLYOSVGWQOS-UHFFFAOYSA-N
Pubchem ID :	15555354

Safety of [ 57508-48-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 57508-48-2 ]

* 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.

Downstream synthetic route of [ 57508-48-2 ]

[ 57508-48-2 ] Synthesis Path-Downstream 1~35

1
[ 57508-48-2 ]
[ 1218-69-5 ]
[ 38370-06-8 ]

References: [1]Helvetica Chimica Acta,1972,vol. 55,p. 1566 - 1595.

2
[ 57508-48-2 ]
[ 1972-28-7 ]
[ 26154-49-4 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 3792 - 3795.

3
[ 542-08-5 ]
[ 126597-33-9 ]
[ 57508-48-2 ]
2-Amino-6-methyl-4-(9-oxo-9H-xanthen-4-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-isopropyl ester [ No CAS ]

References: [1]Il Farmaco,1993,vol. 48,p. 1491 - 1502.

4
[ 29816-99-7 ]
[ 126597-33-9 ]
[ 57508-48-2 ]
2-Amino-6-methyl-4-(9-oxo-9H-xanthen-4-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-prop-2-ynyl ester [ No CAS ]

References: [1]Il Farmaco,1993,vol. 48,p. 1491 - 1502.

5
[ 1118-84-9 ]
[ 126597-33-9 ]
[ 57508-48-2 ]
allyl ethyl 1,4-dihydro-2-amino-(xanthen-9-one-4-yl)-6-methyl-3,5-pyridindicarboxylate [ No CAS ]

References: [1]Il Farmaco,1993,vol. 48,p. 1491 - 1502.

6
[ 23022-83-5 ]
[ 57508-48-2 ]
[ 111222-44-7 ]

References: [1]Synthesis,1987,p. 272 - 274.

7
[ 1056246-70-8 ]
[ 57508-48-2 ]
[ 111222-46-9 ]

References: [1]Synthesis,1987,p. 272 - 274.

8
[ 57508-48-2 ]
[ 115550-22-6 ]
[ 116796-69-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 4819 - 4828.

9
[ 57508-48-2 ]
[ 115550-25-9 ]
2-Amino-5-(bis-allyloxy-phosphoryl)-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester; hydrochloride [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 4819 - 4828.

10
[ 57508-48-2 ]
[ 115550-23-7 ]
[ 116796-70-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 4819 - 4828.

11
[ 57508-48-2 ]
[ 116796-68-0 ]
2-Amino-5-(bis-allyloxy-phosphoryl)-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester; hydrochloride [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 4819 - 4828.

12
[ 57508-48-2 ]
[ 107431-60-7 ]
3-nitrooxypropyl 2-amino-3-ethoxycarbonyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-pyridinecarboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 108 - 116.

13
[ 126597-33-9 ]
[ 57508-48-2 ]
[ 141-97-9 ]
2-Amino-6-methyl-4-(9-oxo-9H-xanthen-4-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Il Farmaco,1993,vol. 48,p. 1491 - 1502.

14
[ 126597-33-9 ]
[ 57508-48-2 ]
[ 105-45-3 ]
2-Amino-6-methyl-4-(9-oxo-9H-xanthen-4-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester [ No CAS ]

References: [1]Il Farmaco,1993,vol. 48,p. 1491 - 1502.

15
[ 57508-48-2 ]
[ 2114-00-3 ]
[ 111222-43-6 ]

References: [1]Synthesis,1987,p. 272 - 274.

16
[ 57508-48-2 ]
[ 70-11-1 ]
[ 111222-40-3 ]

Yield	Reaction Conditions	Operation in experiment
64%		The following is representative: <strong>[57508-48-2]ethyl 3-amino-3-iminopropanoate hydrochloride</strong> (3) (8.3 g, 50.0 mmol) and NaOEt (5.1 g, 75.0 mmol) were dissolved in abs. EtOH at 0 C and stirred for 20 min under argon. The mixture was heated to 60 C, and 2-bromo-1-phenylethanone (4b) (5.0 g, 25.0 mmol) was added portion wise over 5 min. After 1.5 h the mixture was cooled to 20 C and the solvent was evaporated under reduced pressure. The residue was diluted with distilled water (20 mL) and extracted with EtOAc (3 × 80 mL). The organic layer was washed with water (3 × 20 mL) and brine (3 × 20 mL). The combined water fractions were back extracted with EtOAc (2 × 20 mL). The organic phases were dried over MgSO4, and the solvent was evaporated under reduced pressure. Purification was by silica-gel column chromatography (EtOAc/n-pentane, 7/3).
64%		Pyrrolopyrimidines route 1 The following is representative: Ethyl 2-amino-5-phenyl-lH-pyrrole-3-carboxylate (25) Ethyl 3-amino-3-iminopropanoate hydrochloride (23) (8.3 g, 50.0 mmol) and NaOEt (5.1 g, 75.0 mmol) were dissolved in abs. EtOH at 0 C and stirred for 20 min. under argon. The mixture was heated to 60 C, and 2-bromo-l-phenylethanone (24) (5.0 g, 25.0 mmol) was added portion wise over 5 min. After 1.5 h the mixture was cooled to 20 C and the solvent was evaporated under reduced pressure. The residue was diluted with distilled water (20 mL) and extracted with EtOAc (3 X80 mL). The organic layer was washed with water (3 X20 mL) and brine (3 X20 mL). The combined water fractions were back extracted with EtOAc (2X20 mL). The organic phases were dried over MgSC^, and the solvent was evaporated under reduced pressure. Purification was by silica-gel column chromatography (EtOAc/n-pentane, 7/3). This gave 3.7 g (16.1 mmol, 64%) of a beige solid, mp. 101-104 C; 1H NMR (400 MHz, DMSO-<) delta: 10.72 (s, 1H, NH), 7.50-7.44 (m, 2H), 7.32-25 (m, 2H), 7.1 1-7.05 (m, 1H), 6.46 (d, J=2.4, 1H), 5.65 (s, 2H), 4.15 (q, J=6.8, 2H), 1.25 (t, J=6.8, 3H). 13C NMR (100 MHz, DMSO-<), delta: 165.4, 148.6, 132.6, 129.1 (2C), 125.4, 123.6, 122.8 (2C), 104.0, 93.9, 58.6, 15.2. HRMS (ESI): 231.1 124 (calcd C13H14N2O2, 231.1 128, M+H+). IR (neat, cm"1): 3417, 3328, 1662, 1589, 1281 , 1 120, 757, 691.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 6002 - 6014.
[2]Patent: WO2015/959,2015,A1 .Location in patent: Page/Page column 58-59.
[3]Synthesis,1987,p. 272 - 274.

17
[ 57508-48-2 ]
[ 1655-07-8 ]
[ 111655-66-4 ]

References: [1]Zeitschrift fur Chemie,1987,vol. 27,p. 69 - 70.

18
[ 57508-48-2 ]
[ 1775-27-5 ]
[ 111222-45-8 ]

References: [1]Synthesis,1987,p. 272 - 274.

19
[ 57508-48-2 ]
[ 1484-50-0 ]
[ 111222-42-5 ]

References: [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 103 - 112.
[2]Synthesis,1987,p. 272 - 274.

20
[ 57508-48-2 ]
[ 94-05-3 ]
[ 130484-63-8 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1143 - 1151.

21
[ 57508-48-2 ]
[ 814-75-5 ]
[ 111222-41-4 ]

References: [1]Synthesis,1987,p. 272 - 274.

22
[ 27317-59-5 ]
[ 57508-48-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With ammonium chloride; In ethanol; at 120℃; for 1h;Microwave irradiation;	A solution of ethyl 3-amino-3-ethoxypropenoate 10 (760 mg, 4.78 mmol) and NH4Cl (270 mg, 5.0 mmol) in EtOH (4.0 mL) was irradiated in a pressure-rated glass tube (10 mL) at 120 C for 1 h (hold-time) using a CEM Discover microwave synthesizer by moderation of the initial magnetron power (200 W). After cooling in a flow of compressed air, the solution was filtered, evaporated in vacuo and triturated with diethylether to give the title compound1 (923 mg, 78%) as a colourless solid, which was used without further purification; numax (neat) /cm-1 3300, 3095,1738, 1687; deltaH (500 MHz; d6-DMSO) /ppm 9.16 (2H, bs, NHH), 8088 (2H, bs, 2H, NHH), 4.15 (2H, q, J = 7.1 Hz, OCH2), 3.63 (2H, s, 2-H),1.22 (3H, t, J = 7.1 Hz, Me); deltaC (125 MHz, d6-DMSO) /ppm 166.7 (C), 163.6 (C), 61.9 (CH2), 38.2 (CH2), 14.4 (Me); m/z (EI) 130 (M?+).
	With ammonium chloride; In ethanol; for 8h;Heating / reflux;	To anhydrous ethanol (460 g, 10.0 mol) at -3O0C was bubbled in anhydrous hydrogen chloride until the total weight of 821 g of HCl/EtOH solution (44% (w/w) was obtained.Ethyl cyanoacetate (452 g) was added into the HCl/EtOH solution (292 g), the mixture was cooled to ice-salt bath temperature and stirred for 1 hours. The reaction was warmed to room temperature and stood overnight. A white precipitate of 102 was obtained and this mixture was used directly in the next step.The obtained mixture was added to a mixture of ether and a solution OfK2CO3(828 g) in water (2500 mL). The ether layer was separated, dried over Na2SO^ and filtered. The filtrate was concentrated under reduced pressure to give compound 103 (445 g) as a colorless oil.A mixture of compound 103 (445 g) and ammonium chloride (149.5 g) in ethanol(1500 mL) was heated to reflux for 8 h. The solid was isolated and the filtrate was concentrated. The residue was washed with ether and acetone to give product 104 (220 g, 33% total yield in three steps). LCMS: 131 [M+l]+, 1H NMR (DMSO-(Z6): delta 1.22 (t, J = 6.9 Hz, 3H), 3.68 (s, 2H), 4.16 (q, J = 6.9 Hz, 2H), 9.04 (s, 2H), 9.32 (s, 2H).
	With ammonium chloride; In ethanol; for 8h;Heating / reflux;	To anhydrous ethanol (460 g, 10.0 mol) at -3O0C was bubbled in anhydrous hydrogen chloride until the total weight of 821 g of etaCl/EtOeta solution (44% (w/w) was obtained.Ethyl cyanoacetate (452 g) was added into the etaCl/EtOeta solution (292 g), the mixture was cooled to ice-salt bath temperature and stirred for 1 hours. The reaction <n="256"/>was warmed to room temperature and stood overnight. A white precipitate of 102 was obtained and this mixture was used directly in the next step.The obtained mixture was added to a mixture of ether and a solution OfK2COs (828 g) in water (2500 mL). The ether layer was separated, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give compound 103 (445 g) as a colorless oil.A mixture of compound 103 (445 g) and ammonium chloride (149.5 g) in ethanol (1500 mL) was heated to reflux for 8 h. The solid was isolated and the filtrate was concentrated. The residue was washed with ether and acetone to give product 104 (220 g, 33% total yield in three steps). LCMS: 131 [M+l]+, 1H NMR (DMSO-J6): delta 1.22 (t, J= 6.9 Hz, 3H), 3.68 (s, 2H), 4.16 (q, J= 6.9 Hz, 2H), 9.04 (s, 2H), 9.32 (s, 2H).

References: [1]Synlett,2016,vol. 27,p. 1728 - 1732.
[2]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 788 - 796.
[3]Patent: WO2008/33745,2008,A2 .Location in patent: Page/Page column 70.
[4]Patent: WO2008/33747,2008,A2 .Location in patent: Page/Page column 254-255.
[5]European Journal of Medicinal Chemistry,2011,vol. 46,p. 6002 - 6014.

23
[ 27996-87-8 ]
[ 57508-48-2 ]
2-amino-3-ethoxycarbonyl-6-nitroquinoline [ No CAS ]
[ 851266-02-9 ]
diethyl 2,6-diamino-4-(2-fluoro-5-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylate [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,2004,vol. 40,p. 888 - 894.

24
[ 57508-48-2 ]
[ 2632-13-5 ]
[ 173458-92-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium ethanolate; In ethanol; at 0 - 20℃;	To the solution of EtONa (4.08 g, 60 mmol) in EtOH (60 mL) was added compound 104 (10 g, 60 mmol) at 0 0C under nitrogen. The mixture was stirred for 20 minutes and 2-bromo-4'-methyloxy-acetophenone was added. After stirring at room temperature overnight, the mixture was concentrated and the residue was taken up in ethyl acetate, washed with water, brine, dried and concentrated to give a residue which was purified by column chromatography to afford the product 402 as a solid (5.2 g, 67 %yield). 1H NMR (DMSOd6) delta 10.62 (s, IH), 7.41 (d, J = 6.6 Hz, 2H), 6.88 (d, J = 6.6 Hz, 2H), 6.30 (d, J = 3.0 Hz, IH), 5.59 (s, 2H), 4.13 (q, J = 6.9 Hz, 2H), 3.74 (s, 3H), 1.24 (t, J = 7.2 Hz, 3 H). LC-MS: 260 (M+l).
67%		To the solution of EtONa (4.08 g, 60 mmol) in EtOH (60 mL) was added compound 104 (10 g, 60 mmol) at 0 0C under nitrogen. The mixture was stirred for20 minutes and 2-bromo-4'-methyloxy-acetophenone was added. After stirring at room temperature overnight, the mixture was concentrated and the residue was taken up in ethyl acetate, washed with water, brine, dried and concentrated to give a residue which was purified by column chromatography to afford the product 402 as a solid (5.2 g, 67 %yield). 1H NMR (DMSO-d6) delta 10.62 (s, 1eta), 7.41 (d, J = 6.6 Hz,2H), 6.88 (d, J = 6.6 Hz, 2H), 6.30 (d, J = 3.0 Hz, IH), 5.59 (s, 2H), 4.13 (q, J = 6.9 Hz, 2H), 3.74 (s, 3H), 1.24 (t, J = 7.2 Hz, 3 H). LC-MS: 260 (M+l).
		General procedure: The following is representative: <strong>[57508-48-2]ethyl 3-amino-3-iminopropanoate hydrochloride</strong> (3) (8.3 g, 50.0 mmol) and NaOEt (5.1 g, 75.0 mmol) were dissolved in abs. EtOH at 0 C and stirred for 20 min under argon. The mixture was heated to 60 C, and 2-bromo-1-phenylethanone (4b) (5.0 g, 25.0 mmol) was added portion wise over 5 min. After 1.5 h the mixture was cooled to 20 C and the solvent was evaporated under reduced pressure. The residue was diluted with distilled water (20 mL) and extracted with EtOAc (3 × 80 mL). The organic layer was washed with water (3 × 20 mL) and brine (3 × 20 mL). The combined water fractions were back extracted with EtOAc (2 × 20 mL). The organic phases were dried over MgSO4, and the solvent was evaporated under reduced pressure. Purification was by silica-gel column chromatography (EtOAc/n-pentane, 7/3).

References: [1]Magnetic Resonance in Chemistry,2010,vol. 48,p. 244 - 248.
[2]Patent: WO2008/33745,2008,A2 .Location in patent: Page/Page column 65.
[3]Patent: WO2008/33747,2008,A2 .Location in patent: Page/Page column 250.
[4]European Journal of Medicinal Chemistry,2011,vol. 46,p. 6002 - 6014.

25
[ 2318-25-4 ]
[ 57508-48-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 788 - 796.
[2]Letters in drug design and discovery,2014,vol. 11,p. 1143 - 1148.
[3]Synlett,2016,vol. 27,p. 1728 - 1732.

26
[ 105-56-6 ]
ortho-dichlorobenzene(tricarbonyl)chromium [ No CAS ]
[ 57508-48-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 788 - 796.

27
14-bromo-3-(3-nitrobenzylidene)tetradecane-2,4-dione [ No CAS ]
[ 57508-48-2 ]
ethyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-(11-bromo-1-oxo-undecyl)pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In ethanol; ethyl acetate;	D1. Ethyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-(11-bromo-1-oxo-undecyl)pyridine-3-carboxylate 12.7 g of ethyl amidinoacetate hydrochloride and 33.4 g of 14-bromo-3-(3-nitrobenzylidene)tetradecane-2,4-dione are dissolved in 300 ml of ethanol and the solution is treated with 14.5 ml of a 5.25M of sodium methoxide solution. The mixture is heated to boiling under reflux for 7 h and then concentrated in vacuo. The residue is dissolved in ethyl acetate and the solution is washed with water, dried over sodium sulfate, filtered and concentrated again. The oily residue is dried in vacuo and reacted in the next stage without further purification.

References: [1]Patent: US5925642,1999,A .

28
[ 141-52-6 ]
[ 57508-48-2 ]
[ 2632-13-5 ]
[ 173458-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Step 12.1: 2-Amino-3-ethoxycarbonyl-5-(4-methoxy-phenyl)-1H-pyrrole Analogously to Step 8.1, 1.67 g (10 mmol) of 2-amidino-acetic acid ethyl ester hydro-chloride in 20 ml of abs. ethanol are reacted with 716 mg (10 mmol) of sodium ethanolate and 1.145 g (5.0 mmol) of 4-methoxy-phenacyl bromide (Fluka; Buchs/Switzerland) to form the title compound; m.p. 141-142 C.; TLC-Rf =0.4 (hexane/ethyl acetate [1:1]); FAB-MS: (M+H)+ =261.

References: [1]Patent: US6140332,2000,A .

29
[ 31949-21-0 ]
[ 141-52-6 ]
[ 57508-48-2 ]
[ 173458-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Step 10.1: 2-Amino-3-ethoxycarbonyl-5-(2-methoxy-phenyl)-1H-pyrrole Analogously to Step 8.1, 14.5 g (87 mmol) of 2-amidino-acetic acid ethyl ester hydrochloride in 150 ml of abs. ethanol are reacted with 5.9 g (87 mmol) of sodium ethanolate and 10.3 g (44 mmol) of 2-bromo-1-(2-methoxy-phenyl)-ethan-1-one (2-bromo-2'-methoxy-acetophenone; Aldrich; Milwaukee/USA) to form the title compound; m.p.: 128 C.; TLC-Rf =0.25 (hexane/ethyl acetate [2:1]).

References: [1]Patent: US6140332,2000,A .

30
[ 141-52-6 ]
[ 57508-48-2 ]
[ 5000-65-7 ]
[ 173458-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Step 11.1: 2-Amino-3-ethoxycarbonyl-5-(3-methoxy-phenyl)-1H-pyrrole Analogously to Step 8.1, 14.5 g (87 mmol) of 2-amidino-acetic acid ethyl ester hydro-chloride in 150 ml of abs. ethanol are reacted with 5.9 g (87 mmol) of sodium ethanolate and 10.3 g (44 mmol) of 2-bromo-1-(3-methoxy-phenyl)-ethan-1-one (2-bromo-3'-methoxy-acetophenone; Janssen) to form the title compound; m.p. 96-97oC; TLC-Rf =0.2 (hexane/ethyl acetate [2:1]).

References: [1]Patent: US6140332,2000,A .

31
2-bromo-(4-ethoxycarbonyl)-acetophenone [ No CAS ]
[ 141-52-6 ]
[ 57508-48-2 ]
[ 187724-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Step 30.1: 2-Amino-3-ethoxycarbonyl-5-(4-ethoxycarbonyl-phenyl)-1H-pyrrole Analogously to Step 8.1, 4.92 g (29.5 mmol) of 2-amidino-acetic acid ethyl ester hydrochloride in 40 ml of absolute ethanol are reacted with 2.0 g (29.5 mmol) of sodium ethanolate and 4.0 g (14.8 mmol) of 2-bromo-(4-ethoxycarbonyl)-acetophenone to form the title compound; m.p.: 150-151 C.; MS: (M)+ =302.

References: [1]Patent: US6140332,2000,A .

32
[ 5765-44-6 ]
[ 57508-48-2 ]
[ 147440-88-8 ]
ethyl 2-amino-5-cyano-6-methyl-4-(3-phenyl-1,7-naphthyridin-5-yl)-1,4-dihydropyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; acetic acid; In ethanol; ethyl acetate; toluene;	EXAMPLE 1 Ethyl 2-amino-5-cyano-6-methyl-4-(3-phenyl-1,7-naphthyridin-5-yl)-1,4-dihydropyridine-3-carboxylate STR24 2 g (8.5 mmol) of 3-phenyl-1,7-naphthyridine-5-carboxaldehyde are suspended in 20 ml of ethanol and stirred with 0.7 ml (8.5 mmol) of 5-methylisoxazole. A solution of 196 mg of sodium in 14 ml of ethanol is added and the mixture is stirred for 2 hours at 50 C. 1.42 g of ethyl amidinoacetate hydrochloride and 0.51 ml (8.5 mmol) of acetic acid are added and the mixture is boiled for 16 hours. After cooling, 10 g of silica gel are added and the mixture is concentrated in vacuo. The residue is chromatographed on a silica gel column using toluene/ethyl acetate mixtures. After concentration of the pure fractions, the product is crystallized by trituration with ether. 2 g of crystals are obtained.

References: [1]Patent: US5434153,1995,A .

33
[ 10230-68-9 ]
[ 138251-24-8 ]
[ 57508-48-2 ]
ethyl 2-amino-6-methyl-5-nitro-4-(3-phenyl-5-quinolyl)-1,4-dihydropyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol; water; ethyl acetate; toluene;	EXAMPLE 1 Ethyl 2-amino-6-methyl-5-nitro-4- (3-phenyl-5-quinolyl)-1,4-dihydropyridine-3- carboxylate STR18 1.66 g (10 mmol) of ethyl amidinoacetate hydrochloride, 1.8 g (17.5 mmol) of nitroacetone and 820 mg (10 mmol) of sodium acetate are added to 2.33 g (10 mmol) of 3-phenylquinoline-5-carbaldehyde in 20 ml of ethanol, and the mixture is heated at reflux for 30 min. The dark red solution obtained is cooled and concentrated. The residue is dissolved in ethyl acetate/water, the phases are separated, and the ethyl acetate phase is extracted with sodium hydrogen carbonate solution and water, dried and concentrated. The mixture obtained is purified on a silica gel column using toluene/ethyl acetate in a volume ratio of 2:1. The pure fractions are collected and concentrated. By crystallization from acetonitrile, 116 mg of yellow crystals with a melting point of 252-253 C. are obtained.

References: [1]Patent: US5502062,1996,A .

34
3-nitrooxypropyl 2-(3-nitrobenzylidene)acetoacetate [ No CAS ]
[ 57508-48-2 ]
3-nitrooxypropyl 2-amino-3-ethoxycarbonyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-pyridinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium methylate; In ethyl acetate;	EXAMPLE 1 3-Ethyl 5-(3-nitrooxypropyl) 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl) pyridine-3,5-dicarboxylate (Compound No. 30) 400 ml of an ethanolic solution containing 14 g (41 mmoles) of 3-nitrooxypropyl 2-(3-nitrobenzylidene)acetoacetate, 6.9 g (41 mmoles) of ethyl amidinoacetate hydrochloride and 2.24 g (41 mmoles) of sodium methoxide were heated under reflux for 7 hours, The solution was then cooled, insolubles were filtered off and the ethanol was evaporated off under reduced pressure. The resulting residue was dissolved in ethyl acetate and this solution was washed with water and then dried over anhydrous sodium sulfate. The ethyl acetate was evaporated off under reduced pressure, and the resulting residue was subjected to column chromatography through silica gel, eluted with a 2:1 by volume mixture of toluene and ethyl acetate, to give 14.5 g (yield 79%) of the title compound as orange plate-like crystals, melting at 140-141.5 C.

References: [1]Patent: US4992451,1991,A .

35
ethyl ether-ethyl acetate [ No CAS ]
2-(4-benzhydryl-1-piperazinyl)ethyl 2-(3-nitrobenzylidene)acetoacetate [ No CAS ]
[ 57508-48-2 ]
[ 98290-99-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; sodium; In ethanol;	(2) Sodium (0.20 g) was dissolved in dry ethanol (10 ml) and the thus-obtained sodium ethylate solution was added dropwise to a solution of 2-(4-benzhydryl-1-piperazinyl)ethyl 2-(3-nitrobenzylidene)acetoacetate (4.37 g) and ethyl amidinoacetate hydrochloride (1.42 g) in dry ethanol (10 ml) with stirring under reflux over a period of about 15 minutes. The mixture was further refluxed for 5 minutes. The resulting NaCl was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (120 g). From the elude with ethyl ether-ethyl acetate (10:1, v/v), there was obtained 5-[2-(4-benzhydryl-1-piperazinyl)ethyl] 3-ethyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate as a yellow powder. Yield 3.22 g.

References: [1]Patent: US4603135,1986,A .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Heat of Combustion • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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CAS No.: 57508-48-2

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CAS No.: 57508-48-2

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[ 57508-48-2 ] Synthesis Path-Downstream 1~35

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