1-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene → 2-Nitro-3,5-bis(trifluoromethyl)aniline

HRID 53806

Reaction equation

HRID 53806 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[C:6]=1[N+:19]([O-:21])=[O:20])(=O)C>Cl.CCO>[N+:19]([C:6]1[C:7]([C:15]([F:16])([F:17])[F:18])=[CH:8][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:5]=1[NH2:4])([O-:21])=[O:20]

Participants

4

Reactant 1

HCID 199585741-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 199585712-Nitro-3,5-bis(trifluoromethyl)anilineYield 71.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1-acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene (200 mg, 0.63 mmol) in concentrated HCl (3 mL) and EtOH (3 mL) was refluxed overnight, then it was extracted by ethyl acetate (2×3 mL). The extract was dried over Mg2SO4 and evaporated to give 2-nitro-3,5-bis(trifluoromethyl)aniline 123 mg (71%). 1H NMR (DMSO-d6): δ 6.392 (s, 2H), 7.131 (s, 1H), 7.375 (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

Sources & evidence

ORD record
ord-9f6f7fdb7052411baadf954b48407654
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Linked notes

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