Toluene → HCID 23024333, compound

Temperature

120 °C

Aniline (1 ml) and toluene (66 ml) were added to ethyl 3-oxohexanoate (2.1 ml) and stirred at 120° C. overnight. After removing the solvent, sulfuric acid (40 ml) was added to the residue and stirred at 80° C. for seven hours. The reaction solution was put into ice and adjusted to pH=3, and the precipitated crystals were filtered out. Methyl iodide (3 ml), potassium carbonate (1.9 g) and DMF (20 ml) were added to the residue and stirred at room temperature for 26 hours. After removing the solvent, the reaction mixture was diluted with dichloromethane, washed with 1N hydrochloric acid and saturated sodium bicarbonate water and dried over magnesium sulfate to remove the solvent. The residue was purified with a silica gel chromatography (dichloromethane-methanol) to obtain 1-methyl-4-propyl-2(1H)-quinolinone (800 mg).

1. customAfter removing the solvent, sulfuric acid (40 ml)
2. additionwas added to the residue
3. stirringstirred at 80° C. for seven hours
4. filtrationthe precipitated crystals were filtered out
5. additionMethyl iodide (3 ml), potassium carbonate (1.9 g) and DMF (20 ml) were added to the residue
6. stirringstirred at room temperature for 26 hours
7. customAfter removing the solvent
8. additionthe reaction mixture was diluted with dichloromethane
9. washwashed with 1N hydrochloric acid and saturated sodium bicarbonate water
10. dry with materialdried over magnesium sulfate
11. customto remove the solvent
12. customThe residue was purified with a silica gel chromatography (dichloromethane-methanol)

ORD record

ord-649b4d1ff6d3410bb59d15dbec8c2cb1

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07250516B2