Water → Benzoic acid, 3-[(1E)-2-(dimethylamino)ethenyl]-2-nitro-, methyl ester

HRID 1198531Notes

Reaction equation

HRID 1198531 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].N1CCCCC1.O>CN(C)C=O>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 78373Dimethylformamide dimethyl acetalHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Product 1

HCID 771483Benzoic acid, 3-[(1E)-2-(dimethylamino)ethenyl]-2-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-methyl-2-nitrobenzoate (43 g, 0.22 mole), dimethylformamide dimethyl acetal (52.5 g, 0.44 mole) and piperidine (18.7 g, 0.22 mole) in dimethylformamide (120 ml) was heated under reflux for 24 hours, cooled and poured into water to give the crude product.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperaturecooled

Sources & evidence

ORD record
ord-28349c0abea0423eb5800fe16b44b1b2
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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