HCID 178488850, compound → HCID 178488849, compound

Participants

Reaction Steps

5-(3H-Imidazo[4,5-b]pyridin-2-yl)-2-methoxy-nitrobenzene (7.0 g, 26 mmol) was dissolved in 200 mL acetic acid, and zinc powder (35 g, 535 mmol) was added in portions. The zinc was added at such a rate as to keep the temperature of the reaction mixture under 40° C. After complete addition, the reaction mixture was stirred for 3 hours and filtered to give solid. The solids wee washed with water and acetic acid. The filtrate was rotary evaporated in vacuo, and the residue was partitioned between 1 M NaOH and chloroform. The aqueous layer was extracted several times with chloroform, and the combined organic layers were dried over magnesium sulfate, filtered, and rotary evaporated to give 0.71 g of 5-(3H-imidazo[4,5-b]pyridin-2-yl)-2-methoxy-phenylamine as a tan solid. 1H-NMR (CDCl3): δ 8.06 (dd, 1H), 7.66 (dd, 1H), 7.41 (s, 1H), 7.35 (dd, 1H), 6.91 (dd, 1H), 6.64 (d, 1H), 3.67 (s, 3H) ppm. Anal. (C13H12N4O1) C,H,N values were within 0.4% of the theoretical values.

Provenance & Evidence