2-Hydroxyquinoline → 5,6,7,8-tetrahydro-1-(3-methyl-2-butenyl)-5-oxo-2(1H)-quinolinone
Reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[O:11].[H-].[Li+].[CH3:14][CH:15]([CH3:19])[CH:16]=[CH:17]Br.CN(C)C=[O:23]>>[CH3:14][C:15]([CH3:19])=[CH:16][CH2:17][N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:23])[C:5]=2[CH:4]=[CH:3][C:2]1=[O:11]Participants
Procedure
A mixture of 5,6,7,8-tetrahydro-5-oxo-(2(1H)-quinolinone (10.0 g), lithium hydride (0.79), an dimethylformamide (400 ml) was stirred for 3 hrs at 25° C., under nitrogen. 3-Methylbutenyl bromide (10.6 ) was added and the mixture was stirred for an additional eighteen hrs. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was triturated with petroleum ether to afford 10.5 g (74%) of 5,6,7,8-tetrahydro-1-(3-methyl-2-butenyl)-5-oxo-2(1H)-quinolinone.
Workup
- concentrationThe reaction mixture was concentrated
- customthe residue was partitioned between ethyl acetate and water
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe combined organic extracts were washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was triturated with petroleum ether
Sources & evidence
- ORD record
- ord-ecc82a4c81484c64bd3edd1411cba5ff
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05216164
Reaction notes
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