Phosphorus oxychloride → Isoquinoline, 1-chloro-

A solution of isoquinoline-N-oxide (5.52 g, 38 mmol) in dichloromethane (50 ml) was added over 15 minutes to a solution of phosphorus oxychloride (40 ml) in dichloromethane (50 ml) at room temperature. The mixture was stirred for 1 hour, then heated to reflux for 2 hours. After cooling to room temperature, the mixture was poured into ice water (500 ml). The mixture was then extracted with dichloromethane (2×250 ml) and the combined organic layers were washed with 10% aqueous potassium carbonate solution (200 ml), brine (200 ml) then dried (Na2SO4) and evaporated to give the title compound (5.0 g).

1. temperatureheated
2. temperatureto reflux for 2 hours
3. extractionThe mixture was then extracted with dichloromethane (2×250 ml)
4. washthe combined organic layers were washed with 10% aqueous potassium carbonate solution (200 ml), brine (200 ml)
5. dry with materialthen dried (Na2SO4)
6. customevaporated

ORD record

ord-b036090dc2e549a78f27e7912803a8ce

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2