Stannous Chloride → 3-Chloro-5-(thiazol-5-yl)aniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-chloro-5-nitrophenyl)thiazole (0.120 g, 0.499 mmol) inethanol (5 mL) was added tin dichloride (0.9555 g, 4.986 mmol). The mixture was stirred at 90° C. for 1.5 h. After cooling to rt, sat. NaHCO3 (aq) was added dropwise to adjust the pH to 9-10. The resulting suspension was filtered through a Celite pad. The filtrate was concentrated to dryness in vacuo to afford the title compound, which was used directly in the next step without purification. 1H-NMR (CD3OD, 400 MHz): δ=6.67 (t, J=2.0 Hz, 1H), 6.85 (t, J=1.6 Hz, 1H), 6.88 (t, J=1.6 Hz, 1H), 8.10 (s, 1H), 8.94 (s, 1H). MS (ES+): m/z 211.10 (MH+, 35Cl), 213.12 (MH+, 37Cl). HPLC: tR=2.92 min (ZQ2000, polar—5 min).

Provenance & Evidence