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

HRID 442167Notes

Reaction equation

HRID 442167 reaction equation
[CH2:1]([O:8][C:9]([C:11]1C(C2C=CC=C([N+]([O-])=O)C=2)C(C(OC(C)C)=O)=C(C)[NH:15][C:16]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>C(O)(C)C>[CH2:1]([O:8][C:9](=[O:10])/[CH:11]=[C:16](\[NH2:15])/[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 681218262,6-Dimethyl-3-isopropoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester

Product 1

HCID 5368345(Z)-Benzyl 3-aminobut-2-enoateYield 71%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Analogously to Example 1 heating a solution of 75 mmols of 3'-nitrobenzylideneacetoacetic acid isoporpyl ester and 75 mmols of β-aminocrotonic acid benzyl ester in 120 ml of isopropanol gave 2,6-dimethyl-3-isopropoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester of melting point 121° C (from ethanol).

Sources & evidence

ORD record
ord-cc26c141787d4ed8b40d25a846beacc9
Source dataset
uspto-grants-1977_08
Patent number
US04044141

Reaction notes

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