反応 #77499

反応方程式

water NH3

phosphorus oxychloride

HCl

4-[2-(6-methyl-pyridin-3-yl)-ethyl]-2H-isoquinolin-1-one

→

1-chloro-4-[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline

溶媒

EtOAc

dioxane

acetonitrile

反応条件

後処理

1. 1
   その他the water phase is separated
2. 2
   抽出extraction
3. 3
   洗浄The organic phases are washed with water and brine
4. 4
   乾燥dried (Na2SO4)
5. 5
   濃縮concentrated by evaporation

実験手順

3.12 g (11.8 mmol) of 4-[2-(6-methyl-pyridin-3-yl)-ethyl]-2H-isoquinolin-1-one in 48 ml of acetonitrile are mixed, whilst excluding air, with 3.7 ml (40 mmol) of phosphorus oxychloride and 6 ml of 4 N HCl in dioxane and stirred for 18 h at 55° C. After cooling to RT, water/NH3 conc. 10:1 (pH=9) and EtOAc are added, the water phase is separated and extraction effected twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form 1-chloro-4-[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline; 1H NMR (DMSO-d6) δ8.3 (m, 3H), 8.09 (s, 1H), 7.94 (t, 1H), 7.83 (t, 1H), 7.56 (d, 1H), 7.15 (d, 1H), 3.30 (t, H2C), 2.94 (t, H2C), 2.40 (s, H3C).

出典