Water → 8-Hydroxy-5,6,7,8-tetrahydroquinoline

Reaction equation

C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=O)C.C([O-])([O-])=O.[K+].[K+].O>CO>[OH:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1

Participants

Procedure

To a solution of 8-acetoxy-5,6,7,8-tetrahydroquinoline (99.2 g) in methanol (450 mL) was added K2CO3 (144 g, 1.04 mol) and the mixture was stirred at room temperature overnight. The mixture was poured into water (500 mL) and extracted with CHCl3 (3×500 mL) and the combined organic extracts were dried (Na2SO4), and concentrated to provide 71.6 g of 8-hydroxy-5,6,7,8-tetrahydroquinoline as a brown oil. A purified sample (silica gel, 25:1 CH2Cl2-CH3OH) exhibited the following spectral properties: 1H NMR (CDCl3) δ 1.75–1.89 (m, 2H), 1.96–2.06 (m, 1H), 2.25–2.33 (m, 1H), 2.74–2.90 (m, 2H), 4.23 (br s, 1H, OH), 4.72 (dd, 1H J=7.8, 6.3 Hz), 7.12 (dd, 1H, J=7.5, 4.8 Hz), 7.41 (d, 1H, J=7.5 Hz), 8.41 (d, 1H, J=4.8 Hz); 13C NMR (CDCl3) δ 19.60, 28.84, 31.27, 68.87, 122.74, 132.19, 137.40, 147.06, 158.50. ES-MS m/z 150 (M+H).