Ammonia → 3-(aminomethyl)-4-(sec-butyl)-6-methylpyridin-2(1H)-one

HRID 85546노트

반응식

HRID 85546 반응식
[CH:1]([C:5]1[CH:10]=[C:9]([CH3:11])[NH:8][C:7](=[O:12])[C:6]=1[C:13]#[N:14])([CH2:3][CH3:4])[CH3:2].N>CO.[Ni]>[CH:1]([C:5]1[CH:10]=[C:9]([CH3:11])[NH:8][C:7](=[O:12])[C:6]=1[CH2:13][NH2:14])([CH2:3][CH3:4])[CH3:2]

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 682102564-Sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile

생성물 1

HCID 674678593-(aminomethyl)-4-(sec-butyl)-6-methylpyridin-2(1H)-one수율 49%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

To a suspension of Raney Ni (10 g) in methanol (50 mL) was added 4-sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile (7 g, 36.8 mmol) followed by methanolic ammonia (200 mL) and the resulting reaction mixture was stirred at room temperature under hydrogen pressure (80 psi) for 18 h. The reaction mixture was filtered through Celite pad and washed with methanol (250 mL). The filtrate was concentrated under reduced pressure to afford the crude product (7 g). The reaction was repeated again under same condition. The crude products were combined and purified by silica gel chromatography (eluent: 8% MeOH in CHCl3, spiked with NH3) and the obtained solid was triturated with diethyl ether (50 mL) and dried under vacuum to afford the title compound as yellow solid (3.5 g, 28%). 1H NMR (DMSO-d6, 400 MHz): δ 0.809-0.774 (t, 3H, J=6.8 Hz), 1.113-1.097 (d, 3H, J=6.4 Hz), 1.504-1.468 (t, 2H, J=7.2 Hz), 2.184 (s, 3H), 2.839-2.822 (d, 1H, J=6.8 Hz), 3.822 (s, 2H), 6.059 (s, 1H), 8.315 (bs, 2H); LCMS (ES+) m/z=195.22 (M+H)

후처리

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through Celite pad
  3. washwashed with methanol (250 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto afford the crude product (7 g)
  6. custompurified by silica gel chromatography (eluent: 8% MeOH in CHCl3, spiked with NH3)
  7. customthe obtained solid was triturated with diethyl ether (50 mL)
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-a37fb40c46bc4d3b9ae997dab3209803
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846935B2

반응 노트

불러오는 중…