N-(4,5-Difluoro-2-nitrophenyl)acetamide → 4,5-Difluoro-2-nitroaniline

HRID 2232638Notes

Reaction equation

HRID 2232638 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9]C(=O)C)=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1>Cl.C(O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

4

Reactant 1

HCID 540127N-(4,5-Difluoro-2-nitrophenyl)acetamide

Product 1

HCID 1571514,5-Difluoro-2-nitroanilineYield 94.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of N-(4,5-difluoro-2-nitrophenyl)acetamide (70 g) in concentrated hydrochloric acid (110 ml) and ethanol (440 ml) was refluxed for 2 hours. The reaction mixture was poured into ice water (1.5 liter) and the resulting precipitate was collected by filtration and washed with chilled water sufficiently to give the title compound (53.2 g) as yellow prisms, mp 109°-109.5° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with chilled water sufficiently

Sources & evidence

ORD record
ord-416bb3868e9742dd9c608a443b00b89b
Source dataset
uspto-grants-1988_11
Patent number
US04788320

Reaction notes

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