5-((3-(3-Pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]-4(1H)-quinolinone
Reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[NH:13][CH:14]=[C:15]2[C:20](=[O:21])OC(C)(C)OC2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:29][O:28][C:27]1[CH:26]=[C:25]2[C:12](=[CH:11][C:10]=1[O:9][CH2:8][CH2:7][CH2:6][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[NH:13][CH:14]=[CH:15][C:20]2=[O:21]Participants
3
Procedure
After refluxing a solution of 5-((3-(3-pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (4.9 g, 12 mmol) in phenyl ether (50 ml) for 1 minute, the mixture was poured into petroleum ether (500 ml). The solid was collected by filtration and purified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column eluting with water/methanol (100/0 increasing to 20/80). After removal of the solvent by evaporation, the purified product was azeotroped with a mixture of ethanol and toluene to give 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-1,4-dihydroquinolin-4-one (1 g, 27%).
Workup
- filtrationThe solid was collected by filtration
- custompurified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column
- washeluting with water/methanol (100/0 increasing to 20/80)
- customAfter removal of the solvent
- customby evaporation
- customthe purified product was azeotroped with a mixture of ethanol and toluene
Sources & evidence
- ORD record
- ord-4a5f5edc0c534d10826b775f1d2539e9
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809097B1
Reaction notes
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