Methyl 3-aminocrotonate → HCID 65862, compound

HRID 652421Notes

Reaction equation

HRID 652421 reaction equation
[CH2:1]([O:10][C:11](=[O:26])[C:12](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)[C:13]([CH3:15])=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:27][O:28][C:29](=[O:34])/[CH:30]=[C:31](\[NH2:33])/[CH3:32]>>[N+:23]([C:19]1[CH:18]=[C:17]([CH:16]2[C:30]([C:29]([O:28][CH3:27])=[O:34])=[C:31]([CH3:32])[NH:33][C:13]([CH3:15])=[C:12]2[C:11]([O:10][CH2:1][CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:26])[CH:22]=[CH:21][CH:20]=1)([O-:25])=[O:24]

Participants

3

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 53807937HCID 53807937, compound

Product 1

HCID 65862HCID 65862, compoundYield 67%

Procedure

3.51 g (10 mM) of 2-(3-nitrobenzylidene)acetoacetic acid cinnamyl ester was mixed with 1.38 g (12 mM) of 3-aminocrotonic acid methyl ester, and heated at 120° for 3 hours. The reaction mixture was separated by silica gel column chromatography, and 3.00 g of cinnamyl methyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (trans) was obtained (yield 67%). This derivative was recrystallized once with methanol.

Workup

  1. temperatureheated at 120° for 3 hours
  2. customThe reaction mixture was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-cfeef668b2054207a973ac81a990547c
Source dataset
uspto-grants-1987_06
Patent number
US04672068

Reaction notes

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