N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide → 4-Fluoro-2-nitro-6-(trifluoromethyl)aniline

HRID 54365Notes

Reaction equation

HRID 54365 reaction equation
C([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:6]=1[C:15]([F:18])([F:17])[F:16])(=O)C>Cl>[NH2:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:6]=1[C:15]([F:18])([F:16])[F:17]

Participants

3

Reactant 1

HCID 10778132N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 2230974-Fluoro-2-nitro-6-(trifluoromethyl)anilineYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-acetamido-5-fluoro-3-nitrobenzotrifluoride (1.50 g, 5.64 mmol) in concentrated HCl (10 mL) was refluxed overnight and it was extracted by ethyl acetate (2×10 mL). The extract was dried over Mg2SO4, and evaporated to give 624 mg of 2-amino-5-fluoro-3-nitrobenzotrifluoride (50%). 1H NMR (CDCl3): δ6.547 (s, 2H), 7.570 (dd, 1H, J1 =2.7 Hz, J2 =5.7 Hz), 8.114 (dd, 1H, J1 =2.7 Hz, J2 =5.7 Hz).

Workup

  1. temperaturewas refluxed overnight
  2. extractionit was extracted by ethyl acetate (2×10 mL)
  3. dry with materialThe extract was dried over Mg2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-54c7cc429f0749e79799657e12743dba
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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