4,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one → 7-Amino-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 24582

Reaction equation

HRID 24582 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[C:5](=[O:15])[CH2:4][CH2:3]1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[C:5](=[O:15])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 134632924,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one2×

Product 1

HCID 154628417-Amino-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 230.0 mg (1.05 mmol) 3,4-dihydro-4,4-dimethyl-7-nitro-naphthalen-1(2H)-one (Compound D8) in 5.0 mL of EtOAc was stirred at room temperature with a catalytic amount of 10% Pd-C under 1 atm of H2 for 24 h. The catalyst was removed by filtration through a pad of Celite, and the filtrate concentrated under reduced pressure to give the title compound as a dark green oil.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-4509abea1889401ab5df860d43263674
Source dataset
uspto-grants-2005_02
Patent number
US06855832B2

Linked notes

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