Ammonium formate → 5-Amino-2,4-di-tert-butylphenol

HRID 1915313Notes

Reaction equation

HRID 1915313 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([N+:15]([O-])=O)=[CH:7][C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:15][C:8]1[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[C:6]([OH:18])[CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 441762252,4-Di-tert-butyl-5-nitrophenol

Product 1

HCID 441762265-Amino-2,4-di-tert-butylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2,4-di-tert-butyl-5-nitro-phenol (1.86 g, 7.4 mmol) and ammonium formate (1.86 g) in ethanol (75 mL) was added Pd-5% wt. on activated carbon (900 mg). The reaction mixture was stirred at reflux for 2 h, cooled to room temperature and filtered through Celite. The Celite was washed with methanol and the combined filtrates were concentrated to yield 5-amino-2,4-di-tert-butyl-phenol as a grey solid (1.66 g, quant.). 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 1H, OH), 6.84 (s, 1H), 6.08 (s, 1H), 4.39 (s, 2H, NH2), 1.27 (m, 18H); HPLC ret. time 2.72 min, 10-99% CH3CN, 5 min run; ESI-MS 222.4 m/z (MH+).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationfiltered through Celite
  3. washThe Celite was washed with methanol
  4. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-060e9509bb5e431e9fd492e36e336b47
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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