1-[3-(tert-Butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanone → 1-[3-Amino-5-(tert-butyl)-4-(methoxymethoxy)phenyl]-1-ethanone

HRID 1295994Notes

Reaction equation

HRID 1295994 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:18](=[O:20])[CH3:19])[CH:8]=[C:9]([N+:15]([O-])=O)[C:10]=1[O:11][CH2:12][O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[C].[Pd]>[NH2:15][C:9]1[CH:8]=[C:7]([C:18](=[O:20])[CH3:19])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[O:11][CH2:12][O:13][CH3:14]

Participants

4

Reactant 1

HCID 589099361-[3-(tert-Butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanone

Product 1

HCID 229296651-[3-Amino-5-(tert-butyl)-4-(methoxymethoxy)phenyl]-1-ethanoneYield 87.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

After adding 10% palladium-carbon (50% wet) (14 g) to a solution of the 1-[3-(tert-butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanone (69.4 g, 247 mmol) in toluene (280 ml) at room temperature, the mixture was hydrogenated for 7 hours under normal pressure. The 10% palladium-carbon was removed by celite filtration and the solvent was distilled off under reduced pressure. The residue was recrystallized from hexane to yield the title compound (54.0 g, 87.1% yield) as light green granular crystals.

Workup

  1. customThe 10% palladium-carbon was removed by celite filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-3f83fd5b86e8429fb0c03897eb5a114d
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…