تفاعل #72680

معادلة التفاعل

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

4-methoxybenzylamine

→

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

المردود 25.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe 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
   أخرىThe solid product that formed
5. 5
   أخرىwas collected
6. 6
   workup.STIRRINGthe solution stirred overnight
7. 7
   ترشيحThe solid was collected by filtration

الإجراء التجريبي

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+).

المصدر