Extracurricular laboratory: Synthetic route of 16091-26-2

The chemical industry reduces the impact on the environment during synthesis 3′-Aminobenzanilide. I believe this compound will play a more active role in future production and life.

Related Products of 16091-26-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16091-26-2, name is 3′-Aminobenzanilide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The solid 5 (0.5 mmol) and quinazoline compound 6 (0.55 mmol) was dissolved in 20 mL of ethyl acetate and 4 mL of DMF. The reaction mixture was stirred for about 48-72 h at 45 oC. The reaction color gradually transformed from pale yellow to orange. The resulting mixture was washed with water (30 mL), dried over Na2SO4, concentrated and purified by flash column chromatography to afford the product 7 (yield 40 to 85%). N-(3-(4-Hydroxy-8-nitroquinazolin-5-ylamino)phenyl)benzamide7a Brown solid; 65% yield, M.p. 264.8-265.3 C IR (KBr): 3419, 2929, 1654, 1597, 1540, 1499, 1454, 1339, 1266, 1098, 890, 829 cm-1; 1H NMR (500 MHz, DMSO-d6): deltappm 6.70-6.72 (d, J = 10 Hz, 1H, ArH), 7.10-7.12 (d, J = 10 Hz, 1H, ArH), 7.25-7.28 (m, 1H, ArH), 7.52-7.56 (m, 3H, ArH), 7.59-7.61 (d, J = 10 Hz, 2H, ArH), 7.94-7.95 (d, J = 5 Hz, 2H, ArH), 8.23-8.24 (d, J = 10 Hz, 1H, ArH), 8.30 (s, 1H, NCH=N), 10.27 (s, 1H, NH), 11.59 (s, 1H, NHC=O), 12.99 (br.s, 1H, OH); 13C NMR (125 MHz, DMSO-d6): deltappm 112.55, 113.55, 115.78, 118.25, 118.53, 129.94, 130.68, 131.59, 133.92, 134.29, 134.74, 137.13, 142.53, 142.99, 150.28, 156.24, 166.48, 167.90; HRMS (TOF ESI-): m/z calcd for C21H15N5O4 [(M-H)-], 400.1051; found, 400.1056

The chemical industry reduces the impact on the environment during synthesis 3′-Aminobenzanilide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Yongqiang; Liu, Feifei; He, Guojing; Li, Ke; Zhu, Changcheng; Yu, Wei; Zhang, Conghai; Xie, Mingjin; Lin, Jun; Zhang, Jihong; Jin, Yi; Bioorganic and Medicinal Chemistry Letters; vol. 29; 23; (2019);,
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