6-Hydroxymethylquinoline → 1,2,3,4-Tetrahydroquinolin-6-ylmethanol

HRID 279238

반응식

HRID 279238 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2>O.[Pt](=O)=O.CO>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2

참가 물질

4

반응물 1

HCID 15143856-Hydroxymethylquinoline

생성물 1

HCID 226628871,2,3,4-Tetrahydroquinolin-6-ylmethanol수율 68.7%

시약·촉매·용매 2

HCID 11139377Platinum dioxide monohydrate촉매HCID 887Methanol용매

실험 절차

6-Hydroxymethylquinoline (1 g, 6.28 mmoles) (prepared by the method of: C. E. Kaslow and W. R. Clark, J. Org. Chem., 1953, 18, 55-58.) and methanol (200 mL) were placed in a Parr bomb and platinum (IV) oxide monohydrate (0.5 g, 2.04 mmoles) was added. The mixture was hydrogenated at 50 psi at 25° C. for 2 h. The catalyst was filtered off and washed with methanol. The combined filtrates were evaporated to dryness and the product was chromatographed on silica gel using 1.5% (10% conc. NH4OH in methanol)dichloromethane as the eluant to give the title compound (0.7044 g, 68%): CIMS: m/z 164.35 (MH+); δH (CDCl3) 1.93 (2H, m, 3-CH2) and 2.76 (2H, t, 4-CH2), 3.30 (2H, m, 2-CH2), 4.50 (2H, s, CH2OH), 6.45 (1H, d, Ar—H8), 6.96 ppm (2H, m, Ar—H5 and Ar—H7); δC (CDCl3) CH2: 22.1, 27.0, 42.0, 65.6; CH: 114.2, 126.4, 129.2; C: 121.5, 129.4, 144.5.

후처리

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. washwashed with methanol
  4. customThe combined filtrates were evaporated to dryness
  5. customthe product was chromatographed on silica gel using 1.5% (10% conc. NH4OH in methanol)dichloromethane as the eluant

출처 및 근거

ORD 기록
ord-98935e77f2184c0ebc2b9efb39883832
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362188B1

연결된 노트

불러오는 중…