Some common heterocyclic compound, 114344-60-4, name is 2-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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. name: 2-Amino-3-bromobenzonitrile
3-Bromo-2-[1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrileThe 4-methoxy-1-(4-methoxybenzyl)-1,5-dihydro-pyrrol-2-one (11.19 g, 48.0 mmol), 2-amino-3-bromobenzonitrile (11.83 g, 60.1 mmol), and p-toluene sulfonic acid (8.22 g, 43.2 mmol) were mixed together, ground to fine powder and transferred to a round-bottomed flask. The flask was placed in a preheated 130 C. oil bath and the reaction stirred for 40 minutes. The reaction mixture was removed from the bath, cooled, and dissolved in methylene chloride. The solution was washed with sodium bicarbonate (saturated aqueous solution) and the organic layer dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a brown solid (19.5 g). The crude material was purified by flash chromatography on silica gel eluting with a gradient of 20 to 40% ethyl acetate in methylene chloride to afford the desired compound (6.58 g, 34%). 1H NMR (300.132 MHz, DMSO) delta 9.10 (s, 1H), 8.07 (dd, J=8.1, 1.3 Hz, 1H), 7.92 (dd, J=7.7, 1.2 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.15 (dt, J=8.6, 2.3 Hz, 2H), 6.91 (dt, J=8.9, 2.3 Hz, 2H), 4.44-4.37 (m, 3H), 3.88 (s, 2H), 3.74 (s, 3H). MS APCI, m/z=398/400 (M+H). HPLC 1.94 min.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 114344-60-4, its application will become more common.
Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts