Naphth-1-ylmethylideneacetoacetic acid ethyl ester → 2-Pyrrolidino-6-methyl-4-naphth-1-yl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1077035Notes

Reaction equation

HRID 1077035 reaction equation
C(OC(=O)[CH2:5][C:6]([CH:8]=[CH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)=O)C.[CH2:21]([O:23][C:24](=[O:33])[CH:25]=[C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[NH2:27])[CH3:22]>C(O)C>[CH2:21]([O:23][C:24]([C:25]1[CH:9]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH:8]([C:24]([O:23][CH2:21][CH3:22])=[O:33])[C:6]([CH3:5])=[N:27][C:26]=1[N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:33])[CH3:22]

Participants

4

Reactant 2

HCID 54218022Naphth-1-ylmethylideneacetoacetic acid ethyl esterHCID 706080083-Pyrrolidino-3-aminoacrylic acid ethyl ester

Product 1

HCID 706077502-Pyrrolidino-6-methyl-4-naphth-1-yl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Boiling a solution of 13.4 g of naphth-1-ylmethylideneacetoacetic acid ethyl 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-naphth-1-yl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 121°C (ethanol). Yield: 52% of theory.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-1fa800d546ff42c78faf5136dfab8fa2
Source dataset
uspto-grants-1976_05
Patent number
US03959292

Reaction notes

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