N-[4-fluoro-2-nitro-5-(trifluoromethyl)phenyl]acetamide → 5-Amino-2-fluoro-4-nitrobenzotrifluoride

HRID 53789Notes

Reaction equation

HRID 53789 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:8]([F:14])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=O)C>Cl.CCO>[NH2:4][C:5]1[CH:6]=[C:7]([C:15]([F:18])([F:16])[F:17])[C:8]([F:14])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 1

HCID 10015744N-[4-fluoro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 27376865-Amino-2-fluoro-4-nitrobenzotrifluorideYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 3-acetamido-6-fluoro-4-nitrobenzotrifluoride (593 mg, 2.23 mmol) in concentrated HCl (5 mL) and EtOH (5 mL) was refluxed overnight and it was extracted by ethyl acetate (2×5 mL). The extract was dried over Mg2SO4 and evaporated to give 328 mg (66%) of 3-amino-6-fluoro-4-nitrobenzotrifluoride. 1H NMR (CDCl3): δ 6.105 (S, 2H); 7.110 (d, 1H, J=6.0 Hz); 7.979 (d, 1H, J=10.2 Hz).

Workup

  1. temperaturewas refluxed overnight
  2. extractionit was extracted by ethyl acetate (2×5 mL)
  3. dry with materialThe extract was dried over Mg2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-0dc01dd24ff941e5871ba116414523ae
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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