Methanol → Methyl 4-chloronicotinate

Participants

Reaction Steps

To a solution of 4-chloronicotinic acid (0.5 g, 3.17 mmol) in CH2Cl2 (60 mL) was added oxalyl chloride (1.007 g, 7.93 mmol) dropwise at room temperature followed by the addition of DMF (0.4 mL). The solution was stirred at room temperature for 3 h. Methanol (1.9 mL, 46.8 mmol) was added dropwise and the clear solution was further stirred for 30 min. The solvent was evaporated under reduced pressure to yield methyl 4-chloronicotinate (0.67 g, 3.90 mmol, 50% yield). LCMS (ESI) m/e 172.5 [(M+H)+, calcd for C7H7ClNO2 172.0]; LCMS retention time (Method D): tR=1.15 min.

Provenance & Evidence