Trimethylsilyldiazomethane → Methyl 6-chloro-5-nitronicotinate

Participants

Reaction Steps

(Trimethylsilyl)diazomethane (8.25 mL of a 2.00 M solution in hexanes, 16.5 mmol) was added in three portions to a stirred solution of 6-chloro-5-nitronicotinic acid (1.00 g, 4.95 mmol) in methanol (12.0 mL) and DCM (24.0 mL) at 0° C. The reaction mixture was quenched with TPA and concentrated in vacuo to afford the title compound i-2a. m/z (ES) 217 (MH)+. 1H NMR (500 MHz, CDCl3): δ 9.20 (d, 1H, J=2.1 Hz), 8.79 (d, 1H, J=2.1 Hz), 4.05 (s, 3H).

Provenance & Evidence