Reference of 72235-58-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a solution of 4-chloro-3-fluorobenzylamine (225 muIota_, 1 .83 mmol) and pyridine (296 muIota_, 3.66 mmol) in dichloromethane (5 ml), ethyl 2-chloro-2-oxoacetate (215 1 .92 mmol) was added dropwise over an ice bath. The solution was removed from the ice bath after 10 minutes and left to warm to room temperature. The reaction mixture was diluted with ethyl acetate, washed with 0.2 N HCI (2x) and saturated NaHC03 (1 x), dried with MgS04, filtered and concentrated in vacuo to give 0.3878 g (82% yield) of ethyl 2-(4-chloro-3- fluorobenzylamino)-2-oxoacetate as a white solid. H NMR (CDCI3, 400 MHz) delta 7.45 (s, 1 H), 7.36 (t, J=7.96 Hz, 1 H), 7.09 (d, J=9.6 Hz, 1 H), 7.02 (d, J=8.3 Hz, 1 H), 4.48 (d, J=6.4 Hz, 2H), 4.35 (q, J=6.9 Hz, 2H), 1.38 (t, J=6.9 Hz, 3H). To a solution of ethyl 2-(4-chloro-3- fluorobenzylamino)-2-oxoacetate (1 19.7 mg, 0.461 mmol) in ethanol (6 ml), 50% hydrazine hydrate (57 muIota_) was added dropwise. The reaction was stirred overnight at room (0128) temperature. The product was filtered from the mixture and dried in vacuo, providing 59.0 mg of A/-(4-chloro-3-fluorobenzyl)-2-hydrazinyl-2-oxoacetamide as a white solid (52% yield). H NMR (DMSO-Qf6, 400 MHz) delta 10.02 (s, 1 H), 9.30 (t, J=6.4 Hz, 1 H), 7.49 (t, J=8.24 Hz, 1 H), 7.24 (dd, J=1 .8, 10.5 Hz, 1 H), 7.08 (dd, J=1.36, 8.24Hz, 1 H), 4.51 (s, 2H), 4.27 (d, J=6.4 Hz, 2H); 3C NMR (DMSO-af6, 100 MHz) delta 160.54, 158.74, 158.40, 156.29, 141 .29, 141 .23, 130.99, 125.08, 125.05, 1 18.36, 1 18.19, 1 16.31 , 1 16.10, 41 .86.
The synthetic route of (4-Chloro-3-fluorophenyl)methanamine has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; EASTERN MICHIGAN UNIVERSITY; LAWRENCE, Daniel, A.; EMAL, Cory; REINKE, Ashley; LI, Shih-hon; (40 pag.)WO2019/23526; (2019); A1;,
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