31643-49-9,Some common heterocyclic compound, 31643-49-9, name is 4-Nitrophthalonitrile, molecular formula is C8H3N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
4-nitrophthalonitrile (1.00 g, 5.78 mmol) and 4-hydroxybenzaldehyde (0.71 g, 5.78 mmol) were dissolved inN,N-dimethylformamide (15 mL) and degassed with argon ina dual-bank vacuum-gas manifold system. After stirring for15 min, finely ground anhydrous potassium carbonate (2 g,14.45 mmol) was added portion-wise within 2 h period withthe efficient stirring. The progress of the reaction was monitoredby TLC using DCM / hexane (3/1) solvent system. Thestirring of the suspension was maintained at room temperaturefor further 24 h. The resulting mixture was poured into aniced-water/acetone mixture (5/1: v/v). The occured precipitatewas collected by filtration, washed several times with ethanoland dried in vacuo. The desired pure compound (1) was obtainedas a yellowish powder in sufficient purity. Yield 1.30 g,90 %. m.p. 154 C. FT-IR (PIKE MIRacleTM ATR) nu max/cm-1: 3105-3041(Ar, C-H), 2805-2764 (OC-H), 2237 (C?N),1691 (C=O), 1587-1506 (Ar, C=C), 1489-1309 (C-C), 1255(Ar-O-Ar), 1209, 1155, 1111, 1087, 950, 858, 839, 821. 1HNMR(CDCl3) delta (ppm) : 10.03 (s, 1H, OCH)), 8.01 (d, 2H,ArH), 7.81 (d, 1H, ArH), 7.41-7.34(m, 2H, ArH), 7.23 (d, 2H,ArH). 13C-NMR (CDCl3) delta (ppm): 190.7, 160.3, 159.1,135.9, 134.1, 132.6, 123.0, 122.9, 120.59, 118.2, 115.3,114.9, 110.6.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitrophthalonitrile, its application will become more common.
Reference:
Article; Sen, Pinar; Atmaca, Goeknur Ya?a; Erdo?mu?, Ali; Dege, Necmi; Genc, Hasan; Atalay, Yusuf; Yildiz, S. Zeki; Journal of Fluorescence; vol. 25; 5; (2015); p. 1225 – 1234;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts