Ammonium formate → 5-Amino-2-(tert-butyl)phenol

HRID 1465148Notes

Reaction equation

HRID 1465148 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 219596172-Tert-butyl-5-nitrophenol

Product 1

HCID 574702095-Amino-2-(tert-butyl)phenolYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2-tert-butyl-5-nitrophenol (C-1-a) (196 mg, 1.0 mmol) in EtOH (10 mL) was added ammonium formate (200 mg, 3.1 mmol), followed by 140 mg of 10% Pd—C. The reaction mixture was refluxed for additional 30 min, cooled to room temperature and filtered through a plug of Celite. The filtrate was concentrated to dryness and purified by column chromatography (20-30% EtOAc-Hexane) to give 2-tert-butyl-5-aminophenol (C-1) (144 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ 8.76 (s, 1H), 6.74 (d, J=8.3 Hz, 1H), 6.04 (d, J=2.3 Hz, 1H), 5.93 (dd, J=8.2, 2.3 Hz, 1H), 4.67 (s, 2H), 1.26 (s, 9H); HPLC ret. time 2.26 min, 10-99% CH3CN, 5 min run; ESI-MS 166.1 m/z (MH+).

Workup

  1. temperatureThe reaction mixture was refluxed for additional 30 min
  2. filtrationfiltered through a plug of Celite
  3. concentrationThe filtrate was concentrated to dryness
  4. custompurified by column chromatography (20-30% EtOAc-Hexane)

Sources & evidence

ORD record
ord-650b106d1c2040fb9fd9942f926f7855
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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