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-e681f966887a4bd288f4263228ddcc41

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723719B1