Ammonium formate → 1-Tert-butyl-2-methoxy-5-(trifluoromethyl)-4-aminobenzene

HRID 74009Notes

Reaction equation

HRID 74009 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([N+:15]([O-])=O)=[CH:7][C:6]=1[O:18][CH3:19])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:12])[F:13])[C:8]([NH2:15])=[CH:7][C:6]=1[O:18][CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574702461-Tert-butyl-2-methoxy-5-(trifluoromethyl)-4-nitrobenzene

Product 1

HCID 574702471-Tert-butyl-2-methoxy-5-(trifluoromethyl)-4-aminobenzeneYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 1-tert-butyl-2-methoxy-5-(trifluoromethyl)-4-nitrobenzene (473 mg, 1.7 mmol) and ammonium formate (473 mg, 7.3 mmol) in EtOH (10 mL) was added 10% Pd—C (200 mg). The mixture was refluxed for 1 h, cooled and filtered through Celite. The solvent was removed by evaporation to give 1-tert-butyl-2-methoxy-5-(trifluoromethyl)-4-aminobenzene (C-18) (403 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 7.19 (s, 1H), 6.14 (s, 1H), 4.02 (bs, 2H), 3.74 (s, 3H), 1.24 (s, 9H).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-7e6ec5ffb7444452a365658ce55d9d8d
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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