反应详情

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.

1. customunder 40° C
2. additionAfter complete addition
3. filtrationfiltered
4. customto give solid
5. washThe solids wee washed with water and acetic acid
6. customThe filtrate was rotary evaporated in vacuo
7. customthe residue was partitioned between 1 M NaOH and chloroform
8. extractionThe aqueous layer was extracted several times with chloroform
9. dry with materialthe combined organic layers were dried over magnesium sulfate
10. filtrationfiltered
11. customrotary evaporated