Hydrochloric Acid → 5-Amino-2-fluorobenzonitrile

Participants

Reaction Steps

To a stirred solution of 45.12 grams (0.2 moles) of stannous chloride dihydrate in 100 ml. of concentrated HCl is added, gradually, 5.44 grams (0.0282 moles) of 2,4-dinitrobenzonitrile. An exothermic reaction takes place with the temperature rising to about 80°. The solution is stirred and allowed to come to room temperature over the course of 2 hours. The mixture is made strongly basic by the addition of a 50% sodium hydroxide solution, with cooling, and extracted with methylene chloride. The CH2Cl2 extracts are dried over anhydrous MgSO4 and the solvent removed. There is obtained 3.0 grams (80%) of a yellow solid melting at 102°-3°. Infrared (mull): 3500, 3350, (NH), 2200 (CN) cm-1.

Provenance & Evidence