Sodium Azide → Methyl 4-azido-2-(trifluoromethyl)nicotinate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-chloro-2-(trifluoromethyl)nicotinate (9.75 g, 40.7 mmol) in DMF (300 mL) is added sodium azide (21.2 g, 326 mmol). The solution is warmed to 45° C. for 3 hours and then to 50° C. for 1 hour. The reaction is diluted with water (300 mL) and extracted with ether-pentane (1:1, ca. 1 L). The organic layer is back extracted with water (3×). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 9.50 g (95%) of the title compound as a brown oil: 1H NMR (400 MHz, CD3OD), 8.651 (d, 1H), 7.603 (d, 1H), 3.878 (s, 3H).

Provenance & Evidence