Sodium Sulfate → (1,2,3,4-Tetrahydroquinolin-2-yl)methanol

HRID 1645237Notes

Reaction equation

HRID 1645237 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH:6]1[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 338259ethyl 1,2,3,4-tetrahydroquinoline-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,2,3,4-Tetrahydroquinoline-2-carboxylic acid ethyl ester (4.75 g, 25 mmol) in THF (5 ml/mmol) was added dropwise at 0° C. to a suspension of LAH (2 eq.) in THF (50 ml). The reaction mixture was stirred for 1 h at RT and then heated for 4 h under reflux. After addition of saturated aqueous Na2SO4 solution, filtration was carried out and the organic solvent was removed in vacuo. The product was purified by column chromatography (silica gel, ethyl acetate/hexane 3:7).

Workup

  1. temperatureheated for 4 h
  2. temperatureunder reflux
  3. customthe organic solvent was removed in vacuo
  4. customThe product was purified by column chromatography (silica gel, ethyl acetate/hexane 3:7)

Sources & evidence

ORD record
ord-150f927b52ad4c9da59635e85197daaf
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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