Extracurricular laboratory: Synthetic route of Methyl 2-(4-aminophenyl)acetate

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39552-81-3, name is Methyl 2-(4-aminophenyl)acetate, A new synthetic method of this compound is introduced below., Product Details of 39552-81-3

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39552-81-3, name is Methyl 2-(4-aminophenyl)acetate, A new synthetic method of this compound is introduced below., Product Details of 39552-81-3

A solution of chloride 19 (992 mg, 5 5 mmol) and aniline 50 (1.99 g, 12.0 mmol) in DMSO (30 mL) was heated at 100 C for 6 h and then 20 C for 16 h. The solution was partitioned between EtOAc (200 mL) and water (200 mL), the organic fraction washed with water (2 x 100 mL), dried, and the solvent evaporated. The residue was chromatographed, eluting with 10% EtOAc/DCM, to give the 1-oxide 51 (1.05 g, 61%) as a yellow solid, mp (EtOAc/DCM) 216-218 C; 1H NMR [(CD3)2SO] delta 10.00 (s, 1 H, NH), 8.24 (d, J = 8 3 Hz, 1 H, H-8″), 7.82 (d, J = 8.4 Hz, 2 H, H-2′, H-6′), 7.79 (dd, J = 8.2, 7.3 Hz, 1 H, H-6″), 7.70 (d, J = 8 2 Hz, 1 H, H-5″), 7.40 (dd, J = 8.3, 7.3 Hz, 1 H, H-7″), 7.22 (d, J = 8 4 Hz, 2 H, H-3′, H-5′), 3.67 (s, 3 H, OCH3), 3.60 (s, 2 H, H-2), 13C NMR [(CD3)2SO] delta 171.7 (C-1), 156.3 (C-3″), 147.9 (C-4a”), 138.1 (C-4′), 135.6 (C-6″), 131.9 (C-8a”), 129.4 (C-2′, C-6′), 128.3 (C-1′), 126.7 (C-5″), 125.5 (C-7″), 119.9 (C-8″), 119.7 (C-3′, C-5′), 51.7 (OCH3), 40.1 (C-2); Anal. calc. for C16H14N4O3: C, 61 9; H, 4.6; N, 18.1; found C, 62 3; H, 4.8; N, 18.1 %.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Auckland Uniservices Limited; EP1468688; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics