Related Products of 19179-31-8,Some common heterocyclic compound, 19179-31-8, name is 3,5-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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.
An oven-dried three-necked flask was sealed with septa and evacuated/backfilled with N2 several times before starting the reaction. To a mixture of 2.5 M n-BuLi in hexane (4.2 mL, 10.45 mmol) and dry THF, maintained at below -70 C, a solution of N,N-diethyl-2-methylbenzamide (1 g, 5.23 mmol) and 3,5-dimethoxybenzonitrile (1.11 g, 6.79 mmol) in dry THF was added dropwise, maintaining the temperature below -60 C. The reaction mixture was stirred at -78 C. The reaction mixture was warmed to room temperature and quenched with water. The resulting mixture was extracted with CH2Cl2, the organic extract washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was then purified by column chromatography (n-hexane:EtOAc = 1:1) to obtain compound 5b as white crystals (1.1 g, 74%). Melting point (mp): 170-173 C. 1H NMR (400 MHz, DMSO-d6): delta 11.56 (s, 1H, NH), 8.21-8.19 (m, 1H, 8-H), 7.75-7.70 (m, 2H, Ar-H), 7.52-7.46 (m, 1H, Ar-H), 7.00 (s, 1H, 4-H), 6.97 (d, J = 2 Hz, 2H, 2,6-(H)2), 6.57 (t, J = 2.2 Hz, 1H, 4-H), 3.83 (s, 6H, 3,5-(OCH3)2).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxybenzonitrile, its application will become more common.