반응 #931703

반응 방정식

dihexylamine

1,2-dihydro-2-oxoquinoline-3-carboxylic acid

N-methylmorpholine

isobutyl chlorocarbonate

→

N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide

수율 75.8%

용매

tetrahydrofuran

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring at −15° C. for 4 hours
2. 2
   농축at room temperature overnight, the reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONthe residue, after addition of ethyl acetate
4. 4
   세척was washed with water, 1N hydrochloric acid
5. 5
   건조a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
6. 6
   기타After removal of the drying agent
7. 7
   여과by filtration
8. 8
   농축the filtrate was concentrated under reduced pressure
9. 9
   기타The residue was recrystallized from hexane

실험 절차

In a mixture of 50 ml of tetrahydrofuran and 250 ml of N,N-dimethylformamide were dissolved 9.46 g of 1,2-dihydro-2-oxoquinoline-3-carboxylic acid and 5.06 g of N-methylmorpholine, and after cooling to −15° C., 6.83 g of isobutyl chlorocarbonate was added dropwise over 10 minutes. After stirring at −15° C. for 10 minutes, 9.73 g of dihexylamine was added dropwise over 5 minutes. After stirring at −15° C. for 4 hours and then at room temperature overnight, the reaction mixture was concentrated under reduced pressure, and the residue, after addition of ethyl acetate, was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane to give 13.51 g of N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide.

출처