In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6609-57-0 as follows. Safety of 2-Ethoxybenzonitrile
2-Ethoxybenzonitrile was prepared from 2-ethoxybenzamide 5 according to the method reported by Nowakowski23 in 89% yield (lit.23 yield 92%); Rf (hexane/EtOAc 9:1) 0.45; nmax (crystal): 2231 cm 1 (C^N). 1H NMR (CDCl3, d ppm): 7.57e7.51 (m, 2H, 4-H and 5-H of C6H4), 7.01 (d, J 7.3 Hz, 1H, 6-H of C6H4), 6.97 (d, J 8.8 Hz, 1H, 3-H of C6H4), 4.17 (q, J 7 Hz, 2H, OCH2), 1.49 (t, J 7.1 Hz, 3H, CH3). Ethyl 2-ethoxybenzimidate hydrochloride was synthesized by passing dry HCl(gas) through the solution of 2- ethoxybenzonitrile in anhydrous ethyl alcohol. This compound was obtained as a white solid (46%); mp 49e54 C; Rf (hexane/ EtOAc 7:3) 0.36. 1H NMR (CDCl3, d ppm): 13.01 (br s, 1H, NH), 10.14 (br s, 1H, NH), 8.04 (dd, J 1.7 and 8 Hz, 1H, 6-H of C6H4), 7.74e7.70 (m, 1H, 4-H of C6H4), 7.18e7.14 (m, 2H, 3-H and 5-H of C6H4), 5.04 (q, J 7 Hz, 2H, NCOCH2), 4.39 (q, J 7 Hz, 2H, OCOCH2), 1.63 (t, J 7.1 Hz, 3H, NCOCH2CH3), 1.57 (t, J 6.8 Hz, 3H, OCOCH2CH3). 2- Ethoxybenzamidine hydrochloride 6 was prepared from ethyl 2- ethoxybenzimidate hydrochloride and NH3/methanol. Crude product was purified by crystallization (methanol/ethyl ether) to provide 6 as a white solid crystal (96%); mp 190e192 C; (lit.24 yield 91%, mp 195e196 C); Rf (n-butanol/acetic acid/water 4:4:1) 0.31; 1H NMR (CDCl3thDMSO-d6, d ppm): 9.76 (br s, 2H, NH), 8.41 (br s, 2H, NH), 7.80 (d, J 7.8 Hz, 1H, 6-H of C6H4), 7.55e7.51 (m, 1H, 4-H of C6H4), 7.06 (t, J 7.6 Hz, 1H, 5-H of C6H4), 7.0 (d, J 8.3 Hz, 1H, 3-H of C6H4), 6.69 (br s, 2H, NH2), 4.15 (q, J 7 Hz, 2H, OCH2), 1.43 (t, J 7.1 Hz, 3H, CH3). nmax (crystal): 1662 cm 1 (C]N). MS (ESI, matrix DHB): [MthH]th found: 165.1. C9H12N2O requires 165.095.
According to the analysis of related databases, 6609-57-0, the application of this compound in the production field has become more and more popular.
Reference:
Article; Olszewska, Teresa; Gajewska, Ewa P.; Milewska, Maria J.; Tetrahedron; vol. 69; 2; (2013); p. 474 – 480;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts