2-Naphthalenecarbonitrile → 1-(2-Naphthyl)methanamine

HRID 638224

Reaction equation

HRID 638224 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)#[N:2].[OH-].[NH4+]>[Ni].C(O)C>[NH2:2][CH2:1][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 119442-NaphthalenecarbonitrileHCID 14923Ammonium Hydroxide

Product 1

HCID 1372821-(2-Naphthyl)methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10.0 g (65.3 mmole) 2-cyanonaphthalene, 2.0 g Raney Nickel, 100 ml ethanol and 9 ml concentrated ammonium hydroxide was hydrogenated at 36 psi (2.53 kg/cm2) for 4.5 days. The mixture was filtered and the filtrate concentrated in vacuo to an oil. The oil was distilled in vacuo to obtain the desired amine as a colorless liquid which solidified on standing. Yield 2.02 g. TLC on silica gel plates showed one spot at Rf 0.1 upon development with 19:1 chloroform/methanol.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo to an oil
  3. distillationThe oil was distilled in vacuo

Sources & evidence

ORD record
ord-b5b1a16b04d347e780fddd3ad427385c
Source dataset
uspto-grants-1985_12
Patent number
US04560690

Linked notes

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