4-CHLORO-3-(OXAZOL-5-YL)ANILINE synthesis

Yield:521983-07-3 500 mg

Reaction Conditions:

with iron;ammonium chloride in methanol;water at 80; for 2 h;

Steps:

28

A suspension of 5-(2-chloro-5-nitrophenyl)-1,3-oxazole (800 mg, 3.6 mmol), Fe powder (806 mg, 14.4 mmol), and NH₄Cl (1.56 g, 28.8 mmol) in MeOH/H₂O (3:2, 15 mL) was stirred at 80 C for 2 hours, cooled to room temperature and filtered. The filtrate was concentrated, extracted with ethyl acetate, dried over anhydrous Na₂SO₄, and concentrated in vacuo. The residue was purified by silica gel column (EA/PE: 1/3) to give 4-chloro-3-(1,3- oxazol-5-yl)aniline (500 mg, 72%) as a white solid.¹H NMR (400 MHz, DMSO-d₆) δ 8.50 (s, 1H), 7.69 (s, 1H), 7.20 (d, J = 9.2 Hz, 1H), 7.03 (d, J = 2.8 Hz, 1H), 6.60 (dd, J = 2.8 Hz, 8.8 Hz, 1H), 5.50 (s, 2H). LC-MS m/z: 195.1 [M+H⁺]. LC-MS Purity (214 nm): > 95%; t_R = 1.58 min.

References:

WO2016/73889,2016,A1 Location in patent:Paragraph 00244