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

HRID 392506

反応式

HRID 392506 の反応式
[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

参加物

4

反応物 1

HCID 12662983(Quinolin-3-yl)methanol

生成物 1

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

試薬・触媒・溶媒 2

HCID 11139377Platinum dioxide monohydrate触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e16c018d4ca043109ef7bae29451ec5d
出典データセット
uspto-grants-2004_10
特許番号
US06800636B2

関連ノート

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