反应详情

A solution of sulphuryl chloride (11.9 ml) in dichloromethane (200 ml) was added dropwise to the solution of 2'-acetyl-6'-fluoro-N-methylformanilide at 0° under a nitrogen atmosphere. The reaction mixture was stirred at 0° for 3.25 hours. Water (100 ml) was added dropwise and the mixture stirred for 30 minutes. The dichloromethane layer was separated, washed with water (160 ml) and dried over magnesium sulphate before removing the solvent under reduced pressure at ambient temperature. The residue was added to a mixture of benzoic acid (22.6 g), potassium carbonate (42.5 g), 25 molecular sieves (4A°, 50 g) and dry dimethylformamide (200 ml) and the resultant mixture stirred at ambient temperature for 3 hours and then at 60° for 2 hours. Further dimethylformamide (600 ml) and potassium carbonate (17 g) were added and the mixture was heated at 60° overnight. The mixture was cooled, filtered and the solvent removed from the filtrate under reduced pressure at 60°. The residue was triturated with water (400 ml) and then with diethyl ether (400 ml). The resultant solid was crystallised from industrial methylated spirit (200 ml) to give the novel compound 8-fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate, m.p. 179°-181°.

1. stirringthe mixture stirred for 30 minutes
2. customThe dichloromethane layer was separated
3. washwashed with water (160 ml)
4. dry with materialdried over magnesium sulphate
5. custombefore removing the solvent under reduced pressure at ambient temperature
6. additionThe residue was added to a mixture of benzoic acid (22.6 g), potassium carbonate (42.5 g), 25 molecular sieves (4A°, 50 g) and dry dimethylformamide (200 ml)
7. stirringthe resultant mixture stirred at ambient temperature for 3 hours
8. waitat 60° for 2 hours
9. additionFurther dimethylformamide (600 ml) and potassium carbonate (17 g) were added
10. temperaturethe mixture was heated at 60° overnight
11. temperatureThe mixture was cooled
12. filtrationfiltered
13. customthe solvent removed from the filtrate under reduced pressure at 60°
14. customThe residue was triturated with water (400 ml)
15. customThe resultant solid was crystallised from industrial methylated spirit (200 ml)