Reaktion #72680

Reaktionsgleichung

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

4-methoxybenzylamine

→

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

Ausbeute 25.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe 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
   SonstigeThe solid product that formed
5. 5
   Sonstigewas collected
6. 6
   workup.STIRRINGthe solution stirred overnight
7. 7
   FiltrationThe solid was collected by filtration

Vorschrift

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+).

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