Carbamimidoyl-acetic acid ethyl ester → 2-Amino-6-methyl-4-(1-naphthyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 2397898Notes

Reaction equation

HRID 2397898 reaction equation
C(O[C:4](=O)[CH2:5][C:6]([CH:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH2:10]1)=O)C.[CH2:20]([O:22][C:23](=[O:28])[CH2:24][C:25](=[NH:27])[NH2:26])[CH3:21]>C(O)C>[CH2:20]([O:22][C:23]([C:24]1[CH:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:6]([C:23]([O:22][CH2:20][CH3:21])=[O:28])=[C:5]([CH3:4])[NH:27][C:25]=1[NH2:26])=[O:28])[CH3:21]

Participants

4

Reactant 2

HCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 70607594(1-Naphthylidene)acetoacetic acid ethyl ester

Product 1

HCID 706032932-Amino-6-methyl-4-(1-naphthyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Boiling a solution of 13.4 g of (1-naphthylidene)acetoacetic acid ethyl ester and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 8 hours yields 2-amino- 6-methyl-4-(1-naphthyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 174° C. (ethanol).

Workup

  1. customfor 8 hours

Sources & evidence

ORD record
ord-3541e39496e04ce1ba02b180d5d3c795
Source dataset
uspto-grants-1977_05
Patent number
US04022898

Reaction notes

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