Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoate → 1,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine

HRID 845257Notes

Reaction equation

HRID 845257 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:5]([CH3:7])=O.[C:19]1(=[O:38])[N:23]([CH2:24][CH2:25][O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30])[C:22](=[O:33])[C:21]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:20]12>C(O)C>[CH3:7][C:5]1[NH:31][C:29]([CH3:30])=[C:28]([C:27]([O:26][CH2:25][CH2:24][N:23]2[C:22](=[O:33])[C:21]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:20]3[C:19]2=[O:38])=[O:32])[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:4]=1[C:3]([O:2][CH3:1])=[O:18]

Participants

4

Reactant 2

HCID 1536427Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoateHCID 67903522HCID 67903522, compound

Product 1

HCID 137998311,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridineYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared by a method analogous to that of Example 1(a) from 14.95 g (60 mmol) of 2-(3-nitrobenzylidene)-acetoacetic acid methyl ester and 16.46 g (60 mmol) of 3-amino-crotonic acid-(2-phthalimidoethyl)ester in ethanol. 25.25 g (83%) of yellow crystals melting at 181°-182° C. are obtained.

Sources & evidence

ORD record
ord-129230c6429042bd9399bdb864461a1d
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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