反应详情

A suspension of 190.0 mg (0.59 mmol) of 3-[2-(4-morpholinyl)ethyl]-8-oxo-5,8-dihydro-3H-imidazo[4,5-g]quinoline-7-carbonitrile, 5.45 mL of 2M oxalyl chloride (in methylene chloride) and 5 drops of DMF is heated at reflux temperature for 1.5 hours. After cooling, the solvent is evaporated to dryness. The residue is cooled in an ice bath and neutralized to pH 7 by slow addition of ice-cooled, aqueous saturated sodium bicarbonate solution. The aqueous solution is extracted with methylene chloride. The organic phase is washed with cold brine and dried over sodium sulfate. Removal of the solvent in vacuo gives the crude product. Purification of the crude product by preparative TLC (developing solvent: 5:95 methanol/methylene chloride) gives 122.8 mg (61%) of the product as a yellow solid, mp 205–207° C.

1. temperatureis heated
2. temperatureat reflux temperature for 1.5 hours
3. temperatureAfter cooling
4. customthe solvent is evaporated to dryness
5. temperatureThe residue is cooled in an ice bath
6. additionneutralized to pH 7 by slow addition of ice-
7. temperaturecooled
8. extractionThe aqueous solution is extracted with methylene chloride
9. washThe organic phase is washed with cold brine
10. dry with materialdried over sodium sulfate
11. customRemoval of the solvent in vacuo
12. customgives the crude product
13. customPurification of the crude product by preparative TLC (developing solvent: 5:95 methanol/methylene chloride)