Water → 1-(4-Methylphenyl)-5-hydroxymethylisoquinoline

HRID 1156901Notes

Reaction equation

HRID 1156901 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([C:18](OCC)=[O:19])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18][OH:19])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 128518431-(4-Methylphenyl)-5-ethoxycarbonylisoquinolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 128518441-(4-Methylphenyl)-5-hydroxymethylisoquinolineYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Methylphenyl)-5-ethoxycarbonylisoquinoline (14.5 g) was dissolved in 200 ml of anhydrous tetrahydrofuran, and with stirring under cooling, lithium aluminum hydride (suspended in 100 ml of tetrahydrofuran) was added dropwise. The mixture was stirred at room temperature for 1 hour. Water and a 20% aqueous solution of sodium hydroxide were added to the reaction mixture, and the mixture was stirred for 30 minutes. The reaction mixture was filtered through Celite. The filtrate was concentrated, and the residue was recrystallized from benzene to afford 7.5 g of 1-(4-methylphenyl)-5-hydroxymethylisoquinoline as colorless needles.

Workup

  1. temperatureunder cooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationThe reaction mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-0b359797df1641de94439a92d334aaa1
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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