Isopropanol → Diethyl 2-amino-4-(2-furyl)-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylate

HRID 918489Notes

Reaction equation

HRID 918489 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:9][C:10]1[O:14][CH:13]=[CH:12][CH:11]=1)[C:6]([CH3:8])=O)[CH3:2].[CH2:16]([O:18][C:19](=[O:24])[CH2:20][C:21](=[NH:23])[NH2:22])[CH3:17].C(O)(C)C>C(O)C>[CH2:16]([O:18][C:19]([C:20]1[CH:9]([C:10]2[O:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])=[C:6]([CH3:8])[NH:22][C:21]=1[NH2:23])=[O:24])[CH3:17]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 252577Ethyl 2-(furan-2-ylmethylidene)-3-oxobutanoateHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 4601376Diethyl 2-amino-4-(2-furyl)-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon boiling a solution of 10.4 g of 2-furfurylideneacetoacetic acid ethyl ester and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 2 hours, 2-amino-6-methyl-4-(fur-2-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 183°C (isopropanol) is obtained. Yield: 78% of theory.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-e03c68f4b79c41f6aad907eff35c7eb3
Source dataset
uspto-grants-1976_07
Patent number
US03971791

Reaction notes

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