Trimethylsilyldiazomethane → Methyl 5,6-Dichloronicotinate

Participants

Reaction Steps

To a solution of 2.15 g (11.2 mmol) of 5,6-dichloronicotinic acid in 10 mL of v:v 1:1 CHCl2/CH3OH at rt was added dropwise 8.4 mL (16.8 mmol) of (trimethylsilyl)diazomethane (2.0 M in hexanes). The mixture was stirred at rt for 30 min and then concentrated. Chromatography on a Biotage 40M cartridge using 1:19 v/v EtOAc/hexanes as the eluant gave 1.85 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 3.98 (s, 3H), 8.35 (d, J=1.8, 1H), 8.88 (d, J=1.8, 1H).

Provenance & Evidence