Diethyl (ethoxymethylene)malonate → 6-methoxy-7-(2-methoxyethoxy)quinolin-4(1H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][O:13][CH3:14].C([O:17][CH:18]=[C:19](C(OCC)=O)[C:20](OCC)=O)C.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][O:13][CH3:14])[NH:7][CH:20]=[CH:19][C:18]2=[O:17]Participants
4
Conditions
- Temperature
- 240 °C
Procedure
A solution of 4-methoxy-3-(2-methoxyethoxy)aniline (5 g, 25.3 mmol) and diethyl ethoxymethylenemalonate (6 ml, 30 mmol) was heated at 110° C. for 30 minutes. Phenyl ether (5 ml) was added and the mixture was heated at 240° C. for 6 hours. The mixture was allowed to cool and diluted with petroleum ether. The resulting solid was collected by filtration and purified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column eluting with acetonitrile/water (40/60) to give 6-methoxy-7-(2-methoxyethoxy)-1,4-dihydroquinolin-4-one (500 mg, 8%).
Workup
- temperatureto cool
- filtrationThe resulting solid was collected by filtration
- custompurified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column
- washeluting with acetonitrile/water (40/60)
Sources & evidence
- ORD record
- ord-e54e8055743f427c9a5296d9d3424d10
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809097B1
Reaction notes
Loading…