(Quinolin-3-yl)methanol → (1,2,3,4-Tetrahydroquinolin-3-yl)methanol

HRID 279235

반응식

HRID 279235 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2>CO.O.[Pt](=O)=O>[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4]1

참가 물질

4

반응물 1

HCID 12662983(Quinolin-3-yl)methanol

생성물 1

HCID 12662987(1,2,3,4-Tetrahydroquinolin-3-yl)methanol수율 83.2%

시약·촉매·용매 2

HCID 11139377Platinum dioxide monohydrate촉매HCID 887Methanol용매

실험 절차

3-Hydroxymethylquinoline (0.45 g, 2.83 mmoles) (prepared as described in: B. R. Brown, D. Ll. Hammick and B. H. Thewlis, J. Chem. Soc., 1951,1145-1149.) was dissolved in methanol (100 mL) and placed in a Parr bomb. Platinum (IV) oxide monohydrate (0.225 g, 0.918 mmoles) was added and the mixture was hydrogenated at 50 psi at 25° C. for 6 h. The catalyst was removed by decantation and washed with methanol. The methanol was evaporated to dryness and the product was chromatographed on silica gel using 3% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (0.3843 g, 83%): CIMS: m/z 164.35 (MH+); δH (CDCl3) 6.50 (1H, d, Ar—H8), 6.64 (1H, t, Ar—H6), 6.98 (1H, d, Ar—H5) and 6.99 ppm(1H, m, Ar—H7); δC (CDCl3) CH2: 29.5, 44.0, 65.2; CH: 34.9, 114.2, 117.4, 126.9, 129.8; C: 120.2, 144.5.

후처리

  1. customThe catalyst was removed by decantation
  2. washwashed with methanol
  3. customThe methanol was evaporated to dryness
  4. customthe product was chromatographed on silica gel using 3% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

출처 및 근거

ORD 기록
ord-8b1dbe4f858143fe96e70307c1821209
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362188B1

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