N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide → 5-Chloro-4-fluoro-2-nitroaniline

HRID 1761642Notes

Reaction equation

HRID 1761642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:12]C(=O)C)[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[F:8]>Cl.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[F:8])[NH2:12]

Participants

4

Reactant 1

HCID 2773811N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

Product 1

HCID 5178355-Chloro-4-fluoro-2-nitroanilineYield 101.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of N-(3-chloro-4-fluoro-6-nitrophenyl)acetamide (30 g) in concentrated hydrochloric acid (50 ml) and ethanol (200 ml) was refluxed for 2.5 hours. To the reaction mixture was added ice water (300 ml) and the resulting precipitate was collected by filtration, washed with water and dried to give the title compound (24.9 g) as yellow needles, mp 149.5°-150° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-5910cdfdf8d448a4a349dea5664d92e6
Source dataset
uspto-grants-1989_05
Patent number
US04826982

Reaction notes

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