Water → HCID 982605, compound

HRID 1587010Notes

Reaction equation

HRID 1587010 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:6]=[C:7]([C:11]([CH3:13])=O)[C:8]([O-:10])=[O:9].[CH3:19][O:20][C:21](=[O:26])/[CH:22]=[C:23](\[NH2:25])/[CH3:24].O.[C:28]1(C)C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]2[C:22]([C:21]([O:20][CH3:19])=[O:26])=[C:23]([CH3:24])[NH:25][C:11]([CH3:13])=[C:7]2[C:8]([O:10][CH3:28])=[O:9])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 643918Methyl 3-aminocrotonateHCID 86746896HCID 86746896, compound

Product 1

HCID 982605HCID 982605, compoundYield 63%

Procedure

A solution of 5.0 g (18.9 mmol) 2-(3,4-dimethoxybenzylidene)acetoacetate and 2.18 g (18.9 mmol) 3-amino-crotonic acid methyl ester in 100 ml toluene was heated in a Dean-Stark apparatus for water removal, the solvent was distilled off from the reaction mixture, and the residue was purified by column chromatography (SiO2 /CHCl3), giving 4.30 g (63%) of dimethyl 1,4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate as whitish yellow crystals. M.P.: 153.5°-155° C.

Workup

  1. distillationthe solvent was distilled off from the reaction mixture
  2. customthe residue was purified by column chromatography (SiO2 /CHCl3)

Sources & evidence

ORD record
ord-ac6d3ac44f974b5b853f7798bf1bfa52
Source dataset
uspto-grants-1993_06
Patent number
US05216172

Reaction notes

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