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 76153-06-5 as follows. Application In Synthesis of 5-Bromo-3-methylbenzene-1,2-diamine
7-bromo-5-methylquinoxaline. To a solution of 5-bromo-3-methylbenzene-1,2-diamine (Bioorg. Med. Chem. 2000, 2591.) (3.63 g, 18.05 mmol) in ethanol (50 ml) was added glyoxal 40 wt. % in water (8.0 ml, 69.7 mmol). The mixture was heated to reflux for 1.5 hours and an aliquot was removed, concentrated and analyzed by LC/MS. Many overlapping peaks were observed, including a major peak corresponding to desired mass 225 ([M+H]+ for 81Br isotope). The mixture was removed from heat and allowed to stir overnight. Reflux was resumed for 1.5 hours and another aliquot was taken. LC/MS showed a higher ratio of desired to other peaks by integration. Analysis after 6 hours showed no appreciable change. The mixture was concentrated to remove most of the ethanol then diluted with water and dichloromethane. The layers were shaken and separated and the aqueous portion was extracted 2* with dichloromethane. Combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give 4.96 g of a black thick residue. The crude material was purified via column chromatography (SiO2) eluding with 10% ethyl acetate/hexane to give the product as a white solid (1.70 g, 7.62 mmol, 42%). 1H NMR (400 MHz, MeOD) delta ppm 8.80-8.84 (2H, m), 8.07 (1H, d, J=2.27 Hz), 7.39 (2H, dd, J=9.07, 5.29 Hz), 7.34 (1H, s), 7.07 (2H, t, J=8.81 Hz), 5.47 (1H, q, J=6.30 Hz), 3.47 (1H, d, J=8.81 Hz), 3.29-3.31 (1H, m), 2.75-2.92 (2H, m), 2.34 (3H, s), 2.31-2.55 (3H, m), 2.07-2.29 (2H, m), 1.96-2.06 (1H, m), 1.36 (3H, d, J=6.30 Hz). Mass 225 [M+H]+ (81Br).
According to the analysis of related databases, 76153-06-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Bristol-Myers Squibb Company; US2009/18163; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary