Methanol → Methyl 4-Chloropicolinate

Temperature

80 °C

Picolinic acid (1) (10 g, 81 mmol) was dissolved in thionyl chloride (40 ml). The reaction mixture was heated to 80° C. and was allowed to stir for 3 days. The reaction mixture was cooled in an ice bath and MeOH (20 ml) was added very slowly. The reaction mixture was allowed to stir for 1 hour, and all solvents were removed under vacuum. The crude product was taken up in ethyl acetate, washed twice with saturated sodium bicarbonate solution, washed with brine and dried over MgSO4. The crude product was purified on silica gel, eluted with 40% ethyl acetate/hexane to yield to the title product 2, a tan crystalline solid (8.1 g (57%), 46.5 mmol). 1H NMR (DMSO-d6): δ 8.72 (d, J=5.2 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 7.83 (dd, J=5.2 Hz, 2.1 Hz, 1H), 3.93 (s, 3H). MS (ESI-POS): [M+H]+=172.

1. temperatureThe reaction mixture was cooled in an ice bath
2. stirringto stir for 1 hour
3. customall solvents were removed under vacuum
4. washwashed twice with saturated sodium bicarbonate solution
5. washwashed with brine
6. dry with materialdried over MgSO4
7. customThe crude product was purified on silica gel
8. washeluted with 40% ethyl acetate/hexane

ORD record

ord-d33cc08d1b3d4859a608cfc0a4fe9986

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07534796B2