Water → 1-Methyl-1,2,3,4-tetrahydro-2-quinolinemethanol
Reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][OH:12].[CH3:13]OS(C)(=O)=O.C(=O)([O-])[O-].[Ca+2].O>CCOCC>[CH3:13][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][OH:12]Participants
Procedure
In 120 ml of ethanol, 6 g of methyl quinaldinate was reduced by hydrogen in the presence of 400 mg of platinum oxide to give 6.8 g of methyl 1,2,3,4-tetrahydroquinaldinate as an oil. 3.0 g of the resulting methylester was further reduced in a dry ether by 1 g of lithium aluminum hydride to give 2.6 g of 1,2,3,4-tetrahydro-2-quinolinemethanol. A mixture of 1.6 g of the resulting alcohol, 0.93 ml of dimethylsulfonic acid, 2.16 g of calcium carbonate and 8 ml of water was stirred at room temperature for 6 hours. To the reaction mixture was added ether and insolubles were removed by filtration. The organic portion was separated, washed with water and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the organic portion was purified by silica gel column chromatography (eluent: chloroform) to give 1.4 g of 1-methyl-1,2,3,4-tetrahydro-2-quinolinemethanol as a pale yellow oil.
Workup
- customwere removed by filtration
- customThe organic portion was separated
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- customAfter removal of the solvent under reduced pressure
- customthe organic portion was purified by silica gel column chromatography (eluent: chloroform)
Sources & evidence
- ORD record
- ord-860533a3ec734132aaa2a289816391c6
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04962096
Reaction notes
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