Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoate → 1,4-Dihydro-2,6-dimethyl-3-ethoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine

HRID 845258Notes

Reaction equation

HRID 845258 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[C:6]([CH3:8])=O)[CH3:2].[C:20]1(=[O:39])[N:24]([CH2:25][CH2:26][O:27][C:28](=[O:33])/[CH:29]=[C:30](\[NH2:32])/[CH3:31])[C:23](=[O:34])[C:22]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:21]12>C(O)C>[CH3:8][C:6]1[NH:32][C:30]([CH3:31])=[C:29]([C:28]([O:27][CH2:26][CH2:25][N:24]2[C:23](=[O:34])[C:22]3=[CH:35][CH:36]=[CH:37][CH:38]=[C:21]3[C:20]2=[O:39])=[O:33])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:19]

Participants

4

Reactant 2

HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateHCID 679035223-Amino-crotonic acid-(2-phthalimido ethyl)ester

Product 1

HCID 135634151,4-Dihydro-2,6-dimethyl-3-ethoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared by a method analogous to that of Example 1(a) from 15.80 g (60 mmol) of 2-(3-nitrobenzylidene)-acetoacetic acid ethyl ester and 16.46 g (60 mmol) of 3-amino-crotonic acid-(2-phthalimidoethyl)ester in ethanol. 27.75 g (89%) of yellow crystals melting at 194°-195° C. are obtained.

Sources & evidence

ORD record
ord-799ad69f58d540a6b6fd8df85bb0bc72
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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