Hexane → Benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine

Participants

Reaction Conditions

Reaction Steps

4-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-2-ol (61.7 gm 197 mmol) was added to phenylphosphonic dichloride (180 mL) and heated to 100° C. in an oil bath, under N2 overnight. The starting material dissolved on heating to give a light yellow solution. Quenched the cooled reaction mixture on to ice water (600 gm of ice+100 mL water) to give a pale yellow solid. Filtered off and washed the solid well with water. The solid was dissolved in ethyl acetate (600 mL) and washed with aqueous sodium hydrogen carbonate solution (10% w/v) until there was no further effervescence and the pH of the aqueous washings were basic. The organic layer was dried over sodium sulphate, filtered and evaporated to give a dirty yellow solid. The solid was dissolved in diethyl ether and to this was added n-hexane until the solution was cloudy, within a few minutes a thick flocculent solid had formed, filtered off, washed with n-hexane and dried to give benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine (60.59 gm 92% yield).

Provenance & Evidence