反应详情

Phosphorous oxychloride (0.6 mL, 6.44 mmol) was reacted with N,N-dimethylformamide then added to a solution of 3-nitro[1,5]naphthyridin-4-ol (1.0 g, 5.23 mmol) in N,N-dimethylformamide (20 mL). The reaction mixture was warmed using a jacketed flask with refluxing acetone as a heat source. After 3 hours the reaction mixture was poured into ice water, isobutylamine (2.0 mL, 20.1 mmol) was added and the mixture was heated on a steam bath. After several hours the reaction mixture was cooled to ambient temperature, filtered and washed with water. The aqueous layer was extracted with dichloromethane. The dichloromethane extract was washed with aqueous sodium bicarbonate, washed with water, dried over magnesium filtrate then loaded onto a layer of silica gel. The silica gel was eluted initially with dichloromethane to remove an impurity then with 5% methanol in dichloromethane to recover the product. The eluant was concentrated to dryness to provide N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine as a solid, m.p. 97-99° C.

1. temperatureThe reaction mixture was warmed
2. additionwas added
3. temperaturethe mixture was heated on a steam bath
4. filtrationfiltered
5. washwashed with water
6. extractionThe aqueous layer was extracted with dichloromethane
7. extractionThe dichloromethane extract
8. washwas washed with aqueous sodium bicarbonate
9. washwashed with water
10. dry with materialdried over magnesium filtrate
11. washThe silica gel was eluted initially with dichloromethane
12. customto remove an impurity
13. customwith 5% methanol in dichloromethane to recover the product
14. concentrationThe eluant was concentrated to dryness