Ethyl 2-(o-nitrobenzylidene)acetoacetate → 2-Carbamoyloxymethyl-6-methyl-4-(o-nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine

HRID 1032569Notes

Reaction equation

HRID 1032569 reaction equation
[C:1]([O:4][CH2:5]/[C:6](/[NH2:13])=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[NH2:2].[N+:14]([C:17]1[CH:32]=[CH:31][CH:30]=[CH:29][C:18]=1[CH:19]=[C:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([O-:16])=[O:15].C(OC(=O)C)C.CCCCCC>C(O)C>[C:1]([O:4][CH2:5][C:6]1[NH:13][C:26]([CH3:28])=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]([C:18]2[CH:29]=[CH:30][CH:31]=[CH:32][C:17]=2[N+:14]([O-:16])=[O:15])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 5250291Ethyl 2-(o-nitrobenzylidene)acetoacetateHCID 21226206Ethyl acetate hexaneHCID 86742112Ethyl 4-carbamoyloxy-3-aminocrotonate

Product 1

HCID 131315882-Carbamoyloxymethyl-6-methyl-4-(o-nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridineYield 58.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.4 g (50 millimoles) of ethyl 4-carbamoyloxy-3-aminocrotonate and 13.2 g (50 millimoles) of ethyl 2-(o-nitrobenzylidene)acetoacetate were dissolved in 200 ml of ethanol and reacted at a temperature of from 60° to 70° C. for 16 hours under stirring. The reaction mixture was concentrated under reduced pressure. The residue was crystallized from ethylacetate-hexane, whereby 12.6 g (yield: 58%) of 2-carbamoyloxymethyl-6-methyl-4-(o-nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine in crystal form was obtained.

Workup

  1. customreacted at a temperature of from 60° to 70° C. for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7fdd54aac81c419e9cb673751753466d
Source dataset
uspto-grants-1990_09
Patent number
US04958024

Reaction notes

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