HCID 59410080, compound → HCID 59410047, compound

HRID 1915461Notes

Reaction equation

HRID 1915461 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[C:8]([N+:13]([O-])=O)=[CH:7][C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[NH2:13][C:8]1[C:9]([CH2:11][CH3:12])=[CH:10][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[C:6]([OH:16])[CH:7]=1

Participants

4

Reactant 1

HCID 59410080HCID 59410080, compound

Product 1

HCID 59410047HCID 59410047, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-4-ethyl-5-nitro-phenol (3.2 g, 14.3 mmol) in methanol (20 mL) was added Raney Nickel (200 mg, 3.4 mmol) under nitrogen atmosphere. The reaction mixture was then stirred overnight at room temperature under an atmosphere of hydrogen (1 atm). The catalyst was removed by filtration through a pad of celite and the filtrate was evaporated under vacuum to give 5-amino-2-tert-butyl-4-ethyl-phenol (1.2 g, 43%). 1H NMR (400 MHz, CDCl3) δ 6.92 (s, 1H), 6.06 (s, 1H), 2.45 (q, J=7.6 Hz, 2H), 1.37 (s, 9H), 1.21 (t, J=7.6 Hz, 3H). MS (ESI) m/e (M+H+) 194.2

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-0c661c518abf465aaefabf713b93e79d
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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