반응 #72680

반응 방정식

4-chloro-2-oxo-1,2-dihydroquinoline-3-carbonitrile

4-methoxybenzylamine

→

4-amino-2-oxo-1,2-dihydroquinoline-3-carbonitrile

수율 25.1%

용매

DMF

반응 조건

후처리

1. 1
   기타the DMF was removed under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in TFA (6 mL)
3. 3
   workup.ADDITIONdichloromethane (10 mL) was added
4. 4
   기타The solid product that formed
5. 5
   기타was collected
6. 6
   workup.STIRRINGthe solution stirred overnight
7. 7
   여과The solid was collected by filtration

실험 절차

4-chloro-2-oxo-1,2-dihydroquinoline-3-carbonitrile (example 72) (0.66 g, 3.23 mmol) was suspended in DMF (7 mL), and 4-methoxybenzylamine (0.94 mL, 7.26 mmol) was added. The reaction was heated at 100° C. for 1 hour and the DMF was removed under vacuum. The residue was dissolved in TFA (6 mL) and stirred at room temperature for 30 minutes and dichloromethane (10 mL) was added. The solid product that formed was collected, suspended in water and the solution stirred overnight. The solid was collected by filtration to give 4-amino-2-oxo-1,2-dihydroquinoline-3-carbonitrile (0.150 g, 25%) as a white solid. M.p.: >250° C. 1H NMR (400 MHz, DMSO-d6) δ7.19 (m, 2H), 7.57 (m, 1H), 7.88 (bs, 2H), 8.12 (d, J=7.6 Hz, 1H), 11.23 (s, 1H). MS 186 (MH+).

출처