반응 #9586

반응 방정식

potassium carbonate

sodium hydrosulfite

tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

→

tert-butyl{4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate

수율 100.5%

용매

water

dichloromethane

water

water

dichloromethane

반응 조건

후처리

1. 1
   기타The layers were separated
2. 2
   추출the aqueous fraction was extracted with dichloromethane
3. 3
   세척washed sequentially with water and saturated aqueous sodium chloride
4. 4
   건조The organic fraction was dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure

실험 절차

Ethyl viologen dibromide (0.069 g, 0.18 mmol), potassium carbonate (12.76 g, 92 mmol) in water (55mL), and sodium hydrosulfite (11.25 g, 65 mmol) in water (55mL) were added sequentially to a solution of tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate (9.0 g, 18.5 mmol) in dichloromethane (110 mL). The resulting biphasic mixture was stirred for 20 hours. The reaction was diluted with water (600 mL) and dichloromethane (500 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined and washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 8.5 g of tert-butyl{4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow-brown amorphous solid.

출처