(5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol → (3-Amino-5-tert-butyl-2-methoxyphenyl)methanol

HRID 243797Notes

Reaction equation

HRID 243797 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-])=O)[C:8]([O:13][CH3:14])=[C:9]([CH2:11][OH:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[NH2:15][C:7]1[C:8]([O:13][CH3:14])=[C:9]([CH2:11][OH:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

Participants

4

Reactant 1

HCID 58493934(5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

Product 1

HCID 58366895(3-Amino-5-tert-butyl-2-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5-tert-butyl-2-methoxy-3-nitrophenyl)methanol (0.250 g, 1.04 mmol) in ethyl acetate (10.4 mL), 10% palladium/activated charcoal (0.025 g) was added and the resulting mixture was stirred at room temperature under hydrogen atmosphere for 14 hours. After completion of the reaction, insoluble materials were filtered through a Celite pad, and the solvent was washed with ethyl acetate. The solvent of the filtrate was evaporated under reduced pressure to obtain 0.219 g (quantitative) of the crude product containing the captioned compound.

Workup

  1. customAfter completion of the reaction, insoluble materials
  2. filtrationwere filtered through a Celite pad
  3. washthe solvent was washed with ethyl acetate
  4. customThe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3b8e79bbc504cba9f693ebbff4c6a6a
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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