Quinoline-6-carbonitrile → 6-(Aminomethyl)quinoline

HRID 1404766Notes

Reaction equation

HRID 1404766 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>N.CO.[Ni]>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 592995Quinoline-6-carbonitrile

Product 1

HCID 15143846-(Aminomethyl)quinolineYield 82%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of quinoline-6-carbonitrile (96 g, 0.62 mol) in saturated ammonia in methanol (1 lit.), Raney-Ni (10 g) was added and the mixture was stirred at 1 atm of H2 at RT for 16 h. The reaction mixture was filtered and the filtrate was concentrated under vacuum to afford the title compound as a brown oil (80 g, 82%). 1H-NMR (δ ppm. DMSO-d6, 400 MHz): δ8.83 (dd, J=4.2, 1.7 Hz, 1H), 8.29 (d, J=8.2, 4.2 Hz, 1H), 3.90 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-eaa7aab09f9842a4b43db2cd1c3878b3
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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