4-(2-Methoxyethoxy)aniline

Synthesis

General procedure for the synthesis of 4-(2-methoxyethoxy)aniline from 4-nitrophenyl-2-methoxyethyl ether: 1-(2-methoxyethoxy)-4-nitrobenzene (38) (3.9 g, 20 mmol), methanol (80 mL), and 10% activated carbon (400 mg) were added to a hydrogenation reactor. The reaction mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the activated carbon. The filtrate was concentrated in vacuum to afford 4-(2-methoxyethoxy)aniline (39) (3.1 g, 93% yield) as a black oily product. m/z (M+1) 168.1 was shown by LC-MS (ESI) analysis.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 21, p. 5177 - 5181
[2] Patent: CN103864792, 2017, B. Location in patent: Paragraph 0313; 0314; 0315; 0316
[3] Patent: WO2015/131080, 2015, A1. Location in patent: Paragraph 00768; 00770
[4] Patent: WO2014/130693, 2014, A1. Location in patent: Paragraph 00544; 00547
[5] European Journal of Medicinal Chemistry, 1980, vol. 15, # 5, p. 399 - 404