Methanol → Methyl 4-Chloropicolinate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence