Phosphorus oxychloride → 2,6-Dichloroquinolin-5-amine

6-Chloro-5-nitroquinoline 1-oxide (4 g) was added to phosphorus oxychloride (15 mL) at 0° C. The solution was allowed to warm to room temperature and stirred for 12 hours. The excess phosphorus oxychloride was evaporated in vacuo and the residue dissolved in water (100 mL)/dichloromethane (100 mL). The layers were separated and the aqueous layer extracted with dichloromethane (2×50 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil. The residue was dissolved in ethanol/water (1:1, 80 mL), ammonium chloride (2.8 g) and iron (2.8 g) added. The mixture was stirred at 65° C. for 4 hours, cooled to room temperature and filtered. The resulting solid was suspended in dimethylsulfoxide (50 mL), methanol (50 mL) and aqueous hydrochloric acid added (2M, 100 mL). The resulting solid was removed by filtration and then treated with ether (50 mL) and isohexane (50 mL). Evaporation of the mixture afforded the sub-title compound as a solid (1 g).

1. customThe excess phosphorus oxychloride was evaporated in vacuo
2. dissolutionthe residue dissolved in water (100 mL)/dichloromethane (100 mL)
3. customThe layers were separated
4. extractionthe aqueous layer extracted with dichloromethane (2×50 mL)
5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give an oil
9. stirringThe mixture was stirred at 65° C. for 4 hours
10. temperaturecooled to room temperature
11. filtrationfiltered
12. additionmethanol (50 mL) and aqueous hydrochloric acid added (2M, 100 mL)
13. customThe resulting solid was removed by filtration
14. additiontreated with ether (50 mL) and isohexane (50 mL)
15. customEvaporation of the mixture

ORD-Eintrag

ord-012e23d57d324f71be509a76c9285fee

Quelldatensatz

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07408065B2