Ethanol → (Z)-Benzyl 3-aminobut-2-enoate

HRID 442176Notes

Reaction equation

HRID 442176 reaction equation
[CH2:1]([O:8][C:9]([C:11]1CC=C[NH:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](O)C>>[CH2:1]([O:8][C:9](=[O:10])/[CH:11]=[C:16](\[NH2:15])/[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 702Ethanol2×HCID 867350251,4-Dihydropyridine-5-carboxylic acid benzyl ester

Product 1

HCID 5368345(Z)-Benzyl 3-aminobut-2-enoateYield 75%

Procedure

Analogously to Example 1 heating a solution of 75 mmols of 2'-trifluoromethylbenzylideneacetoacetic acid methyl ester and 75 mmols of β-aminocrotonic acid benzyl ester in 120 ml of ethanol gave 2,6-dimethyl-3-methoxycarbonyl-4-'2'-trifluoromethylphenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester of melting point 136° C (from ethanol).

Sources & evidence

ORD record
ord-0f539f2ed3974b48814f115f377bce61
Source dataset
uspto-grants-1977_08
Patent number
US04044141

Reaction notes

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