Diethyl ether 2-propanol → 2-Pyrrolidino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-methyl ester

HRID 2163724Notes

Reaction equation

HRID 2163724 reaction equation
COC(=O)C[C:5]([CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:6].[CH2:19]([O:21][C:22](=[O:31])[CH:23]=[C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[NH2:25])[CH3:20].[CH:32]([OH:35])(C)C.[CH3:36][CH2:37]OCC>C(O)C>[CH3:32][O:35][C:5]([CH:7]1[C:36]([CH3:37])=[N:25][C:24]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:23]([C:22]([O:21][CH2:19][CH3:20])=[O:31])[CH:8]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 22147583Diethyl ether 2-propanolHCID 534430103-Nitrobenzylideneacetoacetic acid methyl esterHCID 706080083-Pyrrolidino-3-aminoacrylic acid ethyl ester

Product 1

HCID 706082142-Pyrrolidino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-methyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Boiling a solution of 12.5 g of 3-nitrobenzylideneacetoacetic acid methyl ester and 9.2 g of 3-pyrrolidino-3-aminoacrylic acid ethyl ester in 100 ml of ethanol for 2 hours yields 2-pyrrolidino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-methyl ester of melting point 103° C. (isopropanol/ether).

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-c3dfbb4d71d64649afd839450f807f40
Source dataset
uspto-grants-1979_01
Patent number
US04136187

Reaction notes

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