Dimethylformamide → HCID 23128075, compound

A mixture of 3-allyloxy-7-fluoro-1-methyl-4quinolone, obtained as described in Example 8a, (2.3 g), potassium cyanide (1.0 g), 18-crown-6 ether (5.0 g) and dimethylformamide (200 ml) was stirred at 95° for 2 days. After cooling to ambient temperature, the mixture was poured into water (600 ml) and extracted with dichloromethane (3×150 ml). The combined extracts were washed with water (2×200 ml), dried over magnesium sulphate and the solvent was removed by distillation. The residue was triturated with diethyl ether (50 ml) and the resultant solid added to a mixture of potassium cyanide (1.0 g), 18-crown-6 ether (5.0 g) and dimethylformamide (200 ml). The resultant solution was stirred at 140° for 16 hours and then allowed to cool to 60°. The solvent was removed under reduced pressure at 60° and the residue was partitioned between water (100 ml) and dichloromethane ( 200 ml). The dichloromethane solution was dried over magnesium sulphate and filtered through silica gel (30 g). The filter bed was washed with dichloromethane (5×100 ml) and the combined filtrate and washings were evaporated to give crude 3-allyloxy-7-cyano 1-methyl-4-quinolone.

1. customobtained
2. extractionextracted with dichloromethane (3×150 ml)
3. washThe combined extracts were washed with water (2×200 ml)
4. dry with materialdried over magnesium sulphate
5. customthe solvent was removed by distillation
6. customThe residue was triturated with diethyl ether (50 ml)
7. additionthe resultant solid added to a mixture of potassium cyanide (1.0 g), 18-crown-6 ether (5.0 g) and dimethylformamide (200 ml)
8. stirringThe resultant solution was stirred at 140° for 16 hours
9. temperatureto cool to 60°
10. customThe solvent was removed under reduced pressure at 60°
11. customthe residue was partitioned between water (100 ml) and dichloromethane ( 200 ml)
12. dry with materialThe dichloromethane solution was dried over magnesium sulphate
13. filtrationfiltered through silica gel (30 g)
14. washThe filter bed was washed with dichloromethane (5×100 ml)
15. customthe combined filtrate and washings were evaporated

ORD record

ord-379848930466425aa4ad4653dc2faa4b

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04997840