Water → 2-(Chloromethyl)-3-methoxypyridine

The title compound of Preparation 45 (190 mg, 1.5 mmol) was added to a stirred solution of benzamide (5 mg, 0.4 mmol) in dichloromethane (2 ml) and the mixture heated to reflux temperature. Trichloroisocyanuric acid (190 mg, 0.82 mmol) was added portionwise, then the reaction mixture stirred under reflux for 3 hours, allowed to cool and treated with water (2 ml) and 50% aqueous potassium hydroxide solution (3 ml). The separated aqueous phase was washed with dichloromethane (3×10 ml) and the combined organic solutions dried (Na2SO4) and evaporated under reduced pressure to yield the title compound (180 mg) as a colourless oil. δ (CDCl3): 3.91 (3H, s), 4.76 (2H, s), 7.25 (2H, m), 8.20 (1H, d). LRMS: m/z 158 (M+1)+.

1. temperaturethe mixture heated
2. temperatureto reflux temperature
3. temperatureunder reflux for 3 hours
4. temperatureto cool
5. washThe separated aqueous phase was washed with dichloromethane (3×10 ml)
6. dry with materialthe combined organic solutions dried (Na2SO4)
7. customevaporated under reduced pressure

ORD record

ord-d5117b515d0a4c218ebc8579a00dd843

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06916927B2