Butyl bromide → Methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 14242

Reaction equation

HRID 14242 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Cs+].[CH2:20](Br)[CH2:21][CH2:22][CH3:23]>C1COCC1.CCOC(C)=O>[CH2:20]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 2734983Cesium bicarbonateHCID 16244389Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

Product 1

HCID 21086131Methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylateYield 67.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate (180 mg, 0.94 mmol) and cesium bicarbonate (1.5 g, 4.7 mmol) in THF (2 mL) was added n-butyl bromide (1.0 mL, 9.4 mmol), and the reaction mixture was heated at reflux for 48 h. The reaction mixture was cooled to room temperature, and diluted with EtOAc. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes) afforded methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (156 mg): ESI MS m/z 248 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3aaa66ee44c24706a33c8f1585534b8e
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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