Ethanol → 2-(Acetoxyacetylamino)-6-aminobenzamide

HRID 2248763Notes

Reaction equation

HRID 2248763 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[C:10]=1[C:11]#[N:12])=[O:7])(=[O:3])[CH3:2].C1CCCCC=1.C([OH:28])C>[C].[Pd]>[C:1]([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[C:10]=1[C:11]([NH2:12])=[O:28])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 8079CyclohexeneHCID 149862822-(Acetoxyacetylamino)-6-nitrobenzonitrile

Product 1

HCID 149862792-(Acetoxyacetylamino)-6-aminobenzamide

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a mixture of 2-(acetoxyacetylamino)-6-nitrobenzonitrile (5.7 g) and ethanol (50 ml) are added cyclohexene (10.5 ml) and 10% palladium-carbon (4.7 g). The mixture is refluxed for 20 minutes, and the reaction mixture is cooled to room temperature, and the solid materials are filtered off. The filtrate is distilled under reduced pressure. The residual crude crystals are recrystallized from ethanol to give the title compound (1.2 g) having the following physical properties.

Workup

  1. temperatureThe mixture is refluxed for 20 minutes
  2. filtrationthe solid materials are filtered off
  3. distillationThe filtrate is distilled under reduced pressure
  4. customThe residual crude crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-3ea07f62c85c475d8ad9dfedc7d035e2
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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