Reaktion #77502

Reaktionsgleichung

water NH3

4-[2-(2-methoxy-pyridin-4-yl)-ethyl]-2H-isoquinolin-1-one

phosphorus oxychloride

HCl

→

1-chloro-4-[2-(2-methoxy-pyridin-4-yl)-ethyl]-isoquinoline

Lösungsmittel

EtOAc

acetonitrile

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to RT
2. 2
   Sonstigethe water phase is separated
3. 3
   Extraktionextraction
4. 4
   WaschenThe organic phases are washed with water and brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated by evaporation

Vorschrift

Under a N2 atmosphere, 160 mg (0.57 mmol) of 4-[2-(2-methoxy-pyridin-4-yl)-ethyl]-2H-isoquinolin-1-one in 3.7 ml of acetonitrile are mixed with 131 μl (1.43 mmol) of phosphorus oxychloride and 0.28 ml of 4 N HCl in dioxane and stirred for 7 h at 65° C. After cooling to RT, water/NH3 conc. 10:1 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-(2-methoxy-pyridin-4-yl)-ethyl]-isoquinoline; 1H NMR (DMSO-d6) δ8.30 (d, 1H), 8.27 (d, 1H), 8.13 (s, 1H), 8.03 (d, 1H), 7.94 (t, 1H), 7.85 (t, 1H), 6.90 (d, 1H), 6.73 (s, 1H), 3.80 (s, H3C), 3.32 (t, H2C), 2.95 (t, H2C).

Quelle