Ammonium Hydroxide → Pyrano[2,3-f]quinolin-4-one
Reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([O:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+]>>[O:11]1[C:6]2=[C:5]3[C:10](=[CH:9][CH:8]=[C:7]2[C:14](=[O:16])[CH:13]=[CH:12]1)[N:1]=[CH:2][CH:3]=[CH:4]3Participants
3
Procedure
Polyphosphoric acid (26 ml) was heated at 90°-95° C. and stirred while 3-(5-quinolinoxy)-propionic acid (2.60 g, 0.0120 mole) was added in small portions. After heating for 2 hours the mixture was poured into 200 ml ice water, basified to pH 10 with concentrated ammonium hydroxide and extracted with 3×200 ml ethyl acetate. The combined organic plasma were dried over magnesium sulfate, filtered, and evaporated in vacuo to a solid, which were recrystallized from toluene, m.p. 146°-147° C.
Workup
- additionwas added in small portions
- temperatureAfter heating for 2 hours the mixture
- extractionextracted with 3×200 ml ethyl acetate
- dry with materialThe combined organic plasma were dried over magnesium sulfate