2-Nitroaniline → Acetamide, N-(2-nitrophenyl)-

HRID 1649203Notes

Reaction equation

HRID 1649203 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[C:11]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 69462-NitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 11090Acetamide, N-(2-nitrophenyl)-

Procedure

o-Nitroaniline (300 g, 2.17 mols) was dissolved in acetic anhydride (620 ml) and stirred at 40°-50° C. for 3 hours. The reaction mixture was poured in ice water. Crystals which formed were collected by filtration and dried. o-Acetylaminonitrobenzene thus-obtained was suspended in methanol (2.4 l). After adding 20 g of 10% palladium-carbon, the suspension was subjected to catalytic reduction at room temperature and atmospheric pressure. After completion of reaction, the catalyst was removed by filtration and the solvent was distilled off under reduced pressure to precipitate crystals which then were washed with ethanol and dried over phosphorus pentoxide under reduced pressure to give 248 g of o-aminoacetanilide.

Workup

  1. customCrystals which formed
  2. filtrationwere collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-bc33dd05bf8d4e70a056adb036935ee2
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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