Water → 3-Phenyl-5-hydroxymethylquinoline

HRID 2372822Notes

Reaction equation

HRID 2372822 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([C:17](O)=[O:18])[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[Cl-].[NH4+]>O1CCCC1>[OH:18][CH2:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:8]=[N:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 109886653-Phenyl-quinoline-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 190332423-Phenyl-5-hydroxymethylquinolineYield 106.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 g (0.32 mol) of 3-phenyl-quinoline-5-carboxylic acid are suspended in 1.6 l of abs. tetrahydrfuran under argon and 400 ml of 1 molar lithium aluminum hydride solution in tetrahydrofuran are added dropwise. In this process, the temperature may rise to 35° C. The mixture is subsequently stirred for 90 minutes and 16 ml of water and then 48 ml of saturated ammonium chloride solution are added dropwise with cooling, the mixture is subsequently stirred for 30 minutes and filtered with suction, the solid is washed with tetrahydrofuran and the filtrate is concentrated. About 80 g of crude product are obtained. The melting point of the purified compound is 110°-112° C.

Workup

  1. custommay rise to 35° C
  2. temperaturewith cooling
  3. stirringthe mixture is subsequently stirred for 30 minutes
  4. filtrationfiltered with suction
  5. washthe solid is washed with tetrahydrofuran
  6. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-f040caea5cb74dc09ea6bc0fc6ba34d2
Source dataset
uspto-grants-1992_03
Patent number
US05100900

Reaction notes

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