Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl ester → Ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoate

HRID 255706

Reaction equation

HRID 255706 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10](=[CH:20][N:21]([CH3:23])[CH3:22])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:16][CH:17]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 13281Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl esterHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 54398161Ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoateYield 85.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of ethyl 4-nitrobenzoylacetate (11.9 g) in benzene (100 ml) was dropwise added N,N-dimethylformamide dimethylacetal (9.5 g) dissolved in benzene (50 ml) during a period of 0.5 hour, under stirring at room temperature. The mixture was refluxed for 4 hours. The reaction mixture was evaporated under reduced pressure. The resulting oil was recrystallized from ether-hexane to give 12.5 g of ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoate.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customThe resulting oil was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-15369f39f05943449365882d5b3e604f
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Linked notes

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