반응 #667699

반응 방정식

3-trifluoromethylbenzoic acid

thionyl chloride

3,4-diaminoquinoline

→

4-amino-3-(3-trifluoromethylbenzoylamino)quinoline

수율 98.6%

용매

—

ice water

sodium bicarbonate

hexamethylphosphoramide

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at 0°-5° C. for 3 hours
2. 2
   여과The resulting crystals are filtered
3. 3
   세척washed with water
4. 4
   기타dried

실험 절차

To a solution of 500 mg of 3-trifluoromethylbenzoic acid in 6 ml of anhydrous hexamethylphosphoramide (HMPA) and 0.6 ml of anhydrous acetonitrile is added dropwise 305 mg of thionyl chloride at -5°-0° C. under nitrogen. After stirring at the same temperature for 30 minutes, 380 mg of 3,4-diaminoquinoline is added and stirred at 0°-5° C. for 3 hours. The mixture is diluted with ice-water and neutralized with saturated aqueous sodium bicarbonate. The resulting crystals are filtered, washed with water, and dried to give 780 mg of 4-amino-3-(3-trifluoromethylbenzoylamino)quinoline B1 as a crude product. It is suspended in 15 g of polyphosphoric acid and heated at 120° C. for 4 hours with stirring. The mixture is poured into ice-water and neutralized with 1N sodium hydroxide. The resulting solid is filtered, washed with water and dried. It is chromatographed on silica gel with chloroform-methanol (10:1 v/v) as eluent, yielding 350 mg (47%) of C1 as colorless crystals.

출처