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

HRID 449247

반응식

HRID 449247 반응식
[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

참가 물질

5

반응물 1

HCID 592995Quinoline-6-carbonitrile

생성물 1

HCID 15143846-(Aminomethyl)quinoline수율 82%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 222Ammonia용매HCID 887Methanol용매

실험 절차

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): δ 8.83 (dd, J=4.2, 1.7 Hz, 1H), 8.29 (d, J=8.3 Hz, 1H), 7.95 (d, J=8.6 Hz, 1H), 7.85 (s, 1H), 7.75 (dd J=8.7, 1.8 Hz, 1H), 7.49 (dd, J=8.2, 4.2 Hz, 1H), 3.90 (s, 2H).

후처리

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

출처 및 근거

ORD 기록
ord-da95691567aa4ad0bad8d22f8a7a5c04
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481739B2

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