Phosphorus trichloride (16.96 mL, 1.1 eq.) was slowly added to a solution of N,N-dimethylformamide (329.6 mL) of 5-methyl-2-nitrobenzamide (29.8 g, 0.165 mol) via syringe over a period of 20 minutes. The reaction mixture was stirred at 25 °C for 40 min, followed by heating to 100 °C and continued stirring for 15 min. Upon completion of the reaction, the mixture was slowly poured into ice (750 g) and the pH of the aqueous solution was adjusted to 9-10 with ammonia (75 mL).The aqueous layer was extracted with ethyl acetate (1000 mL, followed by 2 x 600 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-nitro-5-methylbenzonitrile (25.7 g, 96% yield) as a yellow solid, which could be used in subsequent reactions without further purification. The purity of the product was confirmed by 1H NMR: 1H NMR (CDCl3) δ 2.54 (s, 3H, CH3), 7.59 (d, J = 8.4 Hz, 1H, Ar-H), 7.71 (s, 1H, Ar-H), 8.24 (d, J = 8.4 Hz, 1H, Ar-H).
