Nitric Acid → 2-Chloro-4-methyl-6-nitroquinoline

To a solution of 4-methylquinolin-2(1H)-one (11 g, 69 mmol) in concentrated sulfuric acid (100 mL) was added fuming nitric acid (2.7 mL, 80 mol). The temperature of the resulting solution rose to approximately 50°. The reaction mixture was heated at reflux for 1 h, cooled to r.t and carefully poured onto ice. The resulting precipitate was filtered, washed with ice cold water and ether, then dried under vacuum to provide a solid. A mixture of the solid (8.5 g) and phosphorous oxychloride (40 mL) was heated at 100° for 0.45 h at which time the volatiles were removed under vacuum. The residue was cooled in an ice bath. To the cooled mixture was carefully added water (50 mL). The resulting solids were filtered then washed with water and ether and then dried under vacuum to afford the product, MS: m/z 224 (MH+), which was used directly in the next step.

1. customrose to approximately 50°
2. temperatureThe reaction mixture was heated
3. temperatureat reflux for 1 h
4. temperaturecooled
5. additioncarefully poured onto ice
6. filtrationThe resulting precipitate was filtered
7. washwashed with ice cold water and ether
8. customdried under vacuum
9. customto provide a solid
10. temperaturewas heated at 100° for 0.45 h at which time the volatiles
11. customwere removed under vacuum
12. temperatureThe residue was cooled in an ice bath
13. filtrationThe resulting solids were filtered
14. washthen washed with water and ether
15. customdried under vacuum
16. customto afford the product, MS

ORD record

ord-cfe0504a405f4962a2ce31424bdb5876

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084156B2