6-氨基苯酞为胺类衍生物,可用作医药化工合成中间体。具体用于制备6-氨基异苯并呋喃-1(3H)-酮(6-氨基苯酞),如将6-硝基异苯并呋喃-1(3H)-酮在甲醇中溶解,加入钯碳催化剂,在氢气气氛下搅拌过夜,抽滤、浓缩得到目标产物。
医药化工
合成路线 1(1. 合成:57319-65-0)
- 步骤:将6-硝基-1(3H)-异苯并呋喃酮(9.9g,55mmol)溶于四氢呋喃(20ml)-甲醇(60ml)混合溶剂中,加入5%钯-炭催化剂(1.5g);在氢气氛下,室温搅拌20小时;过滤反应混合物,依次用乙酸乙酯和甲醇洗涤固体;合并滤液和洗涤液,减压浓缩;固体用乙酸乙酯洗涤,得到标题化合物(6.21g);浓缩洗涤液,残余物用乙酸乙酯-己烷混合溶剂结晶,得到额外产物(0.95g)。
- 条件:氢气;四氢呋喃-甲醇混合溶剂;20℃;20h;5%钯-炭催化剂。
- 收率:87%。
- 参考文献:[1] Physical Chemistry Chemical Physics, 2005, vol. 7, #24, p. 4070-4081;[2] Chemistry - A European Journal, 2016, vol. 22, #13, p. 4600-4607;[3] ACS Catalysis, 2014, vol. 4, #10, p. 3504-3511;[4] Patent: EP1362856, 2003, A1;[5] Journal of Heterocyclic Chemistry, 2006, vol. 43, #5, p. 1195-1204;[6] Catalysis Letters, 2014, vol. 144, #7, p. 1258-1267;[7] Patent: US2015/51395, 2015, A1;[8] Journal of Heterocyclic Chemistry, 1992, vol. 29, #6, p. 1519-1523;[9] Patent: US2008/9524, 2008, A1;[10] Journal of Organic Chemistry, 2009, vol. 74, #18, p. 6960-6964;[11] Patent: US2015/231142, 2015, A1;[12] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229-238;[13] Chemistry of Heterocyclic Compounds, 2010, vol. 46, #2, p. 140-145;[14] Synthesis (Germany), 2015, vol. 47, #20, p. 3179-3185;[15] Journal of the American Chemical Society, 1937, vol. 59, p. 864;[16] Patent: US2130480, 1935;[17] Chemische Berichte, 1934, vol. 67, p. 675,681;[18] Tetrahedron, 1988, vol. 44, #14, p. 4591-4604;[19] Journal of Medicinal Chemistry, 1993, vol. 36, #22, p. 3417-3423;[20] Patent: US4409017, 1983, A;[21] Bioorganic and Medicinal Chemistry, 2009, vol. 17, #8, p. 3177-3188;[22] Chemical Biology and Drug Design, 2010, vol. 76, #1, p. 25-33;[23] Organic Letters, 2012, vol. 14, #14, p. 3748-3751;[24] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, #4, p. 1063-1069;[25] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, #5, p. 1269-1273;[26] Journal of Medicinal Chemistry, 2015, vol. 58, #9, p. 3997-4015;[27] Bioorganic and Medicinal Chemistry, 2016, vol. 24, #22, p. 5929-5940;[28] European Journal of Organic Chemistry, 2018, vol. 2018, #2, p. 209-214;[29] Applied Catalysis A: General, 2018, vol. 559, p. 127-137;[30] Research on Chemical Intermediates, 2018, vol. 44, #9, p. 5107-5122