7-Nitro-1-tetralone → 7-Amino-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1836275Notes

Reaction equation

HRID 1836275 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 384457-Nitro-1-tetralone

Product 1

HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-oneYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 7-nitro-1-tetralone (2.00 g, 10.5 mmol) in MeOH (20 mL) was treated with 10% Pd-C (100 mg) and hydrogenated at 1 atm for 5 h. Filtration through Celite gave a brown solid (1.38 g). It was suspended in CHCl3 and flash chromatographed over silica gel (69 g) eluting with EtOAc/hexane (1:2) to afford a tan solid (0.62 g, 37% yield): mp 137-138° C.

Workup

  1. filtrationFiltration through Celite

Sources & evidence

ORD record
ord-66577748ff594d7ea67f8ffc8b1c3157
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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