Methyl 3-aminocrotonate → HCID 12896948, compound

HRID 894707Notes

Reaction equation

HRID 894707 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]=[C:7]([C:12]([CH:14]([O:17][CH3:18])[O:15][CH3:16])=O)[C:8]([O:10][CH3:11])=[O:9])([O-:3])=[O:2].[NH2:23]/[C:24](/[CH3:30])=[CH:25]\[C:26]([O:28][CH3:29])=[O:27]>>[CH3:30][C:24]1[NH:23][C:12]([CH:14]([O:17][CH3:18])[O:15][CH3:16])=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]([C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N+:1]([O-:3])=[O:2])[C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

3

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 53644054Methyl 2-(2-nitrobenzylidene)-4,4-dimethoxyacetoacetate

Product 1

HCID 12896948HCID 12896948, compoundYield 60.3%

Procedure

A mixture of methyl 2-(2-nitrobenzylidene)-4,4-dimethoxyacetoacetate (15.19 g) and methyl 3-aminocrotonate (6.50 g) was heated at 60° to 63° C. for 6 hours and at 100° to 105° C. for 4 hours and 45 minutes. The resulting crystalline mass was triturated with methanol and collected by filtration to give crystals of dimethyl 2-methyl-4-(2-nitrophenyl)-6-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (12.04 g). Thus obtained crystals (1.07 g) were recrystallized from methanol (5 ml) to give pure crystals (0.93 g), m.p. 132° to 133° C.

Workup

  1. temperaturewas heated at 60° to 63° C. for 6 hours and at 100° to 105° C. for 4 hours and 45 minutes
  2. customThe resulting crystalline mass was triturated with methanol
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ae466856ab674a5ba152b6db54dffbad
Source dataset
uspto-grants-1981_08
Patent number
US04284634

Reaction notes

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