تفاعل #77499

معادلة التفاعل

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

المذيبات

EtOAc

dioxane

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىthe water phase is separated
2. 2
   استخلاصextraction
3. 3
   غسيلThe organic phases are washed with water and brine
4. 4
   تجفيفdried (Na2SO4)
5. 5
   تركيزconcentrated by evaporation

الإجراء التجريبي

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).

المصدر