939-80-0, A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
Step 5 4-(Cyclohexylcarbamoylmethylamino)-3-nitrobenzonitrile Cyclohexylcarbamoylmethylcarbamic acid benzyl ester (16.359 g) was hydrogenated using 7.5% palladium carbon (3.24 g) in ethanol (164 ml) solution at atmospheric pressure over 8 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. The obtained residue was dissolved in a mixture of ethanol (50 ml) and isopropanol (50 ml). Thereto were added 4-chloro-3-nitrobenzonitrile (8.23 g) and triethylamine (7.1 ml), and the stirred under reflux for 6 hours. After completion of the reaction, water was added under reflux and the mixture was ice-cooled. The resultant solid was collected by filtration and washed successively with water and diisopropyl ether to give the title compound (10.211 g). 1H-NMR (delta ppm, CDCl3) 1.13 (m, 3H), 1.38 (m, 2H), 1.70 (m, 3H), 1.91 (m, 2H), 3.84 (m, 1H), 4.01 (d, J=5.4 Hz, 2H), 5.76 (brd, 1H), 6.81 (d, J=8.7 Hz, 1H), 7.65 (dd, J=2.1, 8.7 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H), 8.81 (brtr, 1H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts