5-METHYL-2-NITROBENZONITRILE

To a solution of 5-methyl-2-nitrobenzamide from (29.8 g, 0.165 mol) in 329.6 mL of N, N-dimethyl formamide was added phosphorous oxychloride (16.96 mL, 1.1 equiv) through syringe over 20 min. at -10° C. The resulting mixture was stirred at 25° C. for 40 minutes, then heated and stirred at 100° C. for 15 minutes. The reaction mixture was poured into ice (750 g) and ammonia (75 mL) was added to the resulting suspension until pH of aqueous solution reached between 9-10. The aqueous layer was extracted with ethyl acetate (1000 mL, 2.x.600 mL). The combined organic layers were dried over sodium sulfate and concentrated to give a yellow solid (25.7 g, 96percent), which was used directly to next step without further purification. 1HNMR spectrum confirmed the presence of substantially pure title compound. 1H NMR (CDCl3): δ 2.54 ppm (s, 3H, CH3), 7.59 (d, J=8.4 Hz, aromatic), 7.71 (s, aromatic), 8.24 (d, J=8.4 Hz, aromatic).A solution of a reaction product as prepared in Step 1 (168 g, 0.93 mol) in dimethylformamide (1 L) was cooled to 0° C. POClGeneral procedure: A mixture of benzaldoxime (121 mg, 1 mmol) and PCC (237 mg, 1.1 mmol) in CHCl3 was heated to reflux for 2 h (monitored by TLC). After the reaction was over, the black reaction mixture was filtered through a Celite pad and washed with EtOAc. Evaporation of the solvent left the crude product, which was purified by column chromatography over silica gel (hexane=EtOAc, 95:5) to afford pure benzonitrile (89 mg, 86percent). The infrared (IR) and 1H and 13C NMR data of this compound are in good agreement with the reported data .

Molecular Weight:162.15
XLogP3:1.8
Hydrogen Bond Acceptor Count:3
Exact Mass:162.042927438
Monoisotopic Mass:162.042927438
Topological Polar Surface Area:69.6
Heavy Atom Count:12
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes