N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide → 4-Chloro-2-nitro-5-(trifluoromethyl)aniline

HRID 439501

Reaction equation

HRID 439501 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:8]([Cl:14])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=O)C>Cl>[NH2:4][C:5]1[CH:6]=[C:7]([C:15]([F:18])([F:16])[F:17])[C:8]([Cl:14])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 1

HCID 22318004N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 27376454-Chloro-2-nitro-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-acetamido-6-chloro-4-nitrobenzotrifluoride (780 mg, 2.76 mmol) in concentrated HCl (3 mL) was refluxed overnight and it was extracted by ethyl acetate (2×3 mL). The extract was dried over Mg2SO4 and evaporated to give 517 mg (78%) of 3-amino-6-chloro-4-nitrobenzofluoride. 1H NMR (CDCl3): δ6.205 (s, 2H); 7.206 (s, 1H); 8.263 (s, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. extractionit was extracted by ethyl acetate (2×3 mL)
  3. dry with materialThe extract was dried over Mg2SO4
  4. customevaporated
  5. customto give 517 mg (78%) of 3-amino-6-chloro-4-nitrobenzofluoride

Sources & evidence

ORD record
ord-fe00b320c4814902abdb28b09a372c54
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Linked notes

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