6-Methylquinoxaline (CAS 6344-72-5) is a high-purity fine chemical intermediate widely used in organic synthesis, pharmaceutical R&D, agrochemical manufacturing and specialty chemical applications.
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Uses & Synthesis Methods
Overview: Quinoxaline and its derivatives are important chemical intermediates and are widely used in the fields of medicine, pesticides, feed, and dyes. In recent years, many research results have shown that 6-methylquinoxaline exhibits certain pharmacological activities in the treatment of obesity, antitumor, and other areas, showing research value and application prospects, attracting considerable attention.
Efficacy and Effects: 6-Methylquinoxaline may bring significant breakthroughs in inhibiting or killing cancer cells, which has also prompted further research into the synthesis and antitumor activity of quinoxaline derivatives.
Production Method:
Starting Materials: 517-21-5 (Glyoxal) 496-72-0 (3,4-Diaminotoluene) 6344-72-5 (6-Methylquinoxaline)
Synthesis of 6-Methylquinoxaline: 3,4-Diaminotoluene (Aldrich, 100 g, 0.82 mol) is dissolved in 600 mL of hot water (70-75°C) and quickly added to a slurry of glyoxal-sodium bisulfite adduct (Aldrich, 239.5 g, 0.9 mol, 1.1 equiv) in 400 mL of water at 60°C. The reaction mixture is heated at 60°C for 1 hour, then an additional 5 g (0.02 mol) of glyoxal adduct is added. After cooling to room temperature, the mixture is filtered through a paper filter. The filtrate is neutralized to pH 7.5-7.8 with 5 M aqueous NaOH and then extracted with diethyl ether (4 × 400 mL). The combined organic phases are dried over anhydrous Na₂SO₄ and concentrated by rotary evaporation to give 92 g of a brown oil. The crude product is purified by vacuum distillation (bp 100-102°C, 10 mmHg; literature value: 86°C, 1 mmHg) to afford 89 g (75% yield) of the desired product as a pale yellow oil.
References: [1] Patent: US2005/282820, 2005, A1. Location in patent: Page/Page column 17-18 [2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 7, p. 803 - 810 [3] Journal of the American Chemical Society, 1947, vol. 69, p. 795,796 |
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