反応 #66921

反応方程式

113

2-(2-Benzyloxyphenyl)-6-morpholinoquinolin-4-one

→

134

収率 81.5%

2-(2-Hydroxyphenyl)-6-morpholinoquinolin-4-one

収率 81.5%

溶媒

MeOH

反応条件

後処理

1. 1
   ろ過The catalyst was filtered off
2. 2
   その他the filtrate was evaporated
3. 3
   その他The crude product was purified by column chromatography (SiO2, CHCl3:MeOH=25:1)

実験手順

To a suspension of 113 (0.4 g, 1.0 mmol) in MeOH (400 ml) was hydrogenated in the presence of 10% Pd/C (0.1 g) at 25□ for 3 h. The catalyst was filtered off and the filtrate was evaporated. The crude product was purified by column chromatography (SiO2, CHCl3:MeOH=25:1) to give 134 as yellow solid. (0.3 g, 0.9 mmol). Yield: 81.5%; mp 290-291° C.; MS (EI, 70 eV): m/z 322.2 (M+); IR (KBr): 1612.56 (C═O), 2969.54 (—NH) cm−1; 1H-NMR (MeOD-d4, 400 MHz) δ 3.30 (m, 4H), 3.87 (m, 4H), 4.48 (s, 1H), 6.64 (s, 1H), 7.02 (d, J=8.8 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H); 7.40 (t, J=8.0 Hz, 1H), 7.60 (d, J=8.8 Hz, 2H), 7.65 (d, J=2.0 Hz, 1H), 7.72 (d, J=9.2 Hz, 1H); Anal. Calcd for C19H18N2O3; C, 70.79; H, 5.63; N, 8.69.

出典