HCID 66632589, compound → 4-methylnaphthalen-1-amine

HRID 1844279Notes

Reaction equation

HRID 1844279 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-])=O)=[CH:4][C:3]=1N>C(O)C.[Ni]>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66632589HCID 66632589, compound

Product 1

HCID 4311874-methylnaphthalen-1-amineYield 96.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-methyl-4-nitro-naphthyl-amine (4.0 g, 21 mmol) in ethanol (300 mL) was added Raney-Nickel (4 scoops). The mixture was stirred under H2 (1 atm) for 16 h. The reaction was filtered through a pad of Celite and concentrated. Purification by silica gel flash column chromatography (EtOAc:Hexanes=15:85) provided product (3.2 g, 75%).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customPurification by silica gel flash column chromatography (EtOAc:Hexanes=15:85)

Sources & evidence

ORD record
ord-35c04156a43345e593217b0a612daf70
Source dataset
uspto-grants-2015_02
Patent number
US08946273B2

Reaction notes

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