반응 #72685

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Triethylamine

phosphorus oxychloride

4-hydroxy-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

→

4-chloro-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

수율 67.0%

용매

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   추출The solution was extracted dichloromethane (2×200 mL
3. 3
   세척washed with water
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (18 mL)
8. 8
   workup.ADDITIONpoured into 200 mL of 30% hexanes in diethyl ether
9. 9
   여과The resultant precipitate was collected by filtration

실험 절차

Triethylamine (5.73 mL, 41.2 mmol) was added to phosphorus oxychloride (60 mL), followed by 4-hydroxy-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide (Example 74c) (6.11 g, 13.7 mmol). The reaction was heated at 65° C. for 4 hours, then cooled to room temperature and carefully poured into ice water (1200 mL). The solution was extracted dichloromethane (2×200 mL. The organic layers were combined and washed with water, dried over MgSO4, filtered and evaporated. The residue was dissolved in dichloromethane (18 mL) and poured into 200 mL of 30% hexanes in diethyl ether. The resultant precipitate was collected by filtration to give crude 4-chloro-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide (4.25 g, 67%) which was used without further purification. MS 463 (MH+).

출처