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

HRID 279238

反応式

HRID 279238 の反応式
[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

参加物

4

反応物 1

HCID 15143856-Hydroxymethylquinoline

生成物 1

HCID 226628871,2,3,4-Tetrahydroquinolin-6-ylmethanol収率 68.7%

試薬・触媒・溶媒 2

HCID 11139377Platinum dioxide monohydrate触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-98935e77f2184c0ebc2b9efb39883832
出典データセット
uspto-grants-2002_03
特許番号
US06362188B1

関連ノート

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