Reaktion #72675

Reaktionsgleichung

Benzyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate

4-methoxybenzylamine

→

benzyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate

Ausbeute 116.5%

Lösungsmittel

TFA

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   SonstigeThe resultant precipitate was collected
3. 3
   workup.DISSOLUTIONdissolved in dichloromethane
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated

Vorschrift

Benzyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 66b) (0.55 g, 1.75 mmol) was dissolved in DMF (8 mL) and 4-methoxybenzylamine (0.56 mL, 4.31 mmol) was added. The reaction was heated at 115° C. for 30 minutes, then cooled to room temperature and poured into ice water. The resultant precipitate was dissolved in 10 mL TFA and stirred at room temperature for 15 minutes, then the mixture was poured into ice water. The resultant precipitate was collected, dissolved in dichloromethane, dried over MgSO4, filtered and evaporated to give the crude benzyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate (600 mg) which was used as this without further purification. MS 295 (MH+).

Quelle