Ethyl acetate hexane → 1-[3-Amino-5-(tert-butyl)-4-hydroxyphenyl]-1-ethanone

HRID 1296012Notes

Reaction equation

HRID 1296012 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([N+:12]([O-])=O)[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.CCCCCC>C(OCC)(=O)C.[C].[Pd]>[NH2:12][C:9]1[CH:8]=[C:7]([C:15](=[O:17])[CH3:16])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:10]=1[OH:11]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 229297281-[3-(Tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone

Product 1

HCID 229299261-[3-Amino-5-(tert-butyl)-4-hydroxyphenyl]-1-ethanoneYield 71.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

After adding 10% palladium-carbon (50% wet) (100 mg) to a solution of 1-[3-(tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone (1.00 g, 4.22 mmol) in ethyl acetate (10 ml) at room temperature, the mixture was hydrogenated for 3 hours under normal pressure. The 10% palladium-carbon was then filtered through celite and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (Wakogel-C200,10 g) to yield the title compound (627 mg, 71.8% yield) as a light red powder from the ethyl acetate-hexane (1:4˜1:3) fraction.

Workup

  1. filtrationThe 10% palladium-carbon was then filtered through celite
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cf3fe3f1f67d42618a9bbc8908a96727
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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