6-Chloroquinoline → 6-Chloro-1,2,3,4-tetrahydroquinoline
反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2>O=[Pt]=O.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2参加物
4
実験手順
A flask filled with a mixture of 6-chloroquinoline (12.0 g, 73.3 mmol), PtO2 (2.16 g, 13 mol %), and MeOH (500 mL, 6.15 M) was flushed with N2 and then equipped with a balloon filled with H2. The reaction was kept under H2 atmosphere and stirred for 4 h. The mixture was filtered through Celite and washed with CH2Cl2. Purification via silica gel chromatography using 50% CH2Cl2 in hexanes gave 6-chloro-1,2,3,4-tetrahydroquinoline (7.7 g, 62%). 1H NMR (400 MHz, DMSO-d6) δ 6.85-6.83 (m, 2H), 6.42-6.39 (m, 1H), 5.82 (s, 1H), 3.17-3.13 (m, 2H), 2.64 (t, J=6.3 Hz, 2H), 1.78-1.72 (m, 2H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=168.2; tR=1.57 min.
後処理
- customwas flushed with N2
- customequipped with a balloon
- additionfilled with H2
- filtrationThe mixture was filtered through Celite
- washwashed with CH2Cl2
- customPurification via silica gel chromatography
出典と根拠
- ORDレコード
- ord-684551fee69d416cb5821c8cecb8d282
- 出典データセット
- uspto-grants-2012_04
- 特許番号
- US08163720B2
反応ノート
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