4-(Pyridin-4-yl)aniline

Uses

4-(4-Pyridinyl)aniline is diazotized, its product is nitrated and reduced to form 2-Amino-4-(4-pyridyl)phenol, which can increase cardiac contractility; Also, it is derived from 4-Pyridineboronic Acid (P991355), which is boronic acid derivative and their binding affinities with diols.

Synthesis

Tert-butyl 4-(pyridin-4-yl)phenylcarbamate (600 mg, 2.2 mmol) was treated with a mixture of dichloromethane (DCM) and trifluoroacetic acid (TFA) (1:1, 1 mL) for 2 hr at room temperature, and upon completion of the reaction, 4-(pyridin-4-yl)aniline (20) (380 mg, 99%) was obtained. Subsequently, the solvent was removed by distillation under reduced pressure. The structure of the product 4-(pyridin-4-yl)aniline (20) was 1H NMR (400 MHz, d6-DMSO) δ 8.81 (s, 2H), 8.25 (s, 2H), 7.76 (d, J = 8.7 Hz, 2H), 6.87 (m, 2H), 2.09 (s, 2H) and mass spectrometry (ESI) m/z 171 [M + H]+ for Confirmation. High resolution mass spectrometry (HRMS) calculated value of CnHn2 171.0917 and measured value of 171.0938 further verified the structure of the product.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[2] Patent: WO2013/112722, 2013, A1. Location in patent: Page/Page column 45
[3] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3542 - 3550