206548-14-3

基本信息
2-氨基-3-甲基-5-溴苯甲酸甲酯
METHYL 2-AMINO-5-BROMO-3-METHYLBENZENECARBOXYLATE
2-Amino-5-bromo-3-methylbenzoic acid methyl ester
Benzoic acid, 2-aMino-5-broMo-3-Methyl-, Methyl ester
Methyl 2-amino-5-bromo-m-toluate, Methyl 5-bromo-3-methylanthranilate
物理化學(xué)性質(zhì)
制備方法

22223-49-0

206548-14-3
以2-氨基-3-甲基苯甲酸甲酯為原料合成2-氨基-5-溴-3-甲基苯甲酸甲酯的一般步驟:將2-氨基-3-甲基苯甲酸甲酯(142.1 g,0.843 mol,純度:98%,定量NMR)溶解于240 mL水中,在30°C下緩慢加入溴化氫(48%水溶液,149.2 g,0.885 mol)。隨后,將所得懸浮液與過氧化氫(30%水溶液,105.1 g,0.927 mol)混合,控制滴加速度使反應(yīng)在2小時內(nèi)完成,并保持反應(yīng)溫度低于70°C。反應(yīng)混合物繼續(xù)攪拌1小時后,分批加入亞硫酸氫鈉(39%水溶液,33.7 g,0.126 mol),直至過氧化物測試呈陰性。用碳酸鈉(0.1當(dāng)量,9.0 g,0.084 mol)分批調(diào)節(jié)反應(yīng)混合物的pH至7-8。經(jīng)過濾和真空干燥后,得到2-氨基-5-溴-3-甲基苯甲酸甲酯,為淺棕色固體。產(chǎn)量:204.2 g,收率:97.7%,純度:98.5%(定量NMR)。1H NMR(600 MHz,d6-DMSO):δ= 7.70(d,1H),7.36(pt,1H),6.63(br s,2H),3.80(s,3H),2.12(s,3H)。
參考文獻:
[1] Patent: US2014/148611, 2014, A1. Location in patent: Paragraph 0066; 0067; 0068
[2] Helvetica Chimica Acta, 2004, vol. 87, # 6, p. 1333 - 1356
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1156 - 1162
[4] Patent: US2015/111870, 2015, A1. Location in patent: Paragraph 0687; 0688
[5] Patent: WO2018/49328, 2018, A1. Location in patent: Page/Page column 26; 27; 28