Water → 3-Methyl-5-hydroxy-5,6,7,8-tetrahydroquinoline

HRID 649178Notes

Reaction equation

HRID 649178 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:12])[C:10]=2[CH:11]=1.[BH4-].[Na+].O>CO>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([OH:12])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5951923-Methyl-7,8-dihydroquinolin-5(6H)-oneHCID 4311764Sodium borohydride

Product 1

HCID 141555773-Methyl-5-hydroxy-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.97 Gram of 7,8-dihydro-3-methylquinolin-5(6H)-one was dissolved in 20 ml of methanol, then to this solution was added 0.23 g of sodium borohydride under ice-cooled condition, the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water, then methanol was removed by evaporation, next extracted with chloroform, and the chloroform extract was dried with anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain 0.98 g of 3-methyl-5-hydroxy-5,6,7,8-tetrahydroquinoline in the form of colorless oily substance.

Workup

  1. temperaturecooled condition
  2. custommethanol was removed by evaporation
  3. extractionnext extracted with chloroform
  4. extractionthe chloroform extract
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-4a0081cc94a845d2aee4c58466b7280e
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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