Sodium Hydroxide → 8-Bromo-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 649175Notes

Reaction equation

HRID 649175 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6](O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.P(Br)(Br)[Br:14].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([Br:14])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 123582223-Methyl-5,6,7,8-tetrahydroquinolin-8-ol

Product 1

HCID 139602608-Bromo-3-methyl-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1.50 Grams of 3-methyl-8-hydroxy-5,6,7,8-tetrahydroquinoline was dissolved in 20 ml of chloroform, to this solution was added dropwise a solution consisting of 1.35 g of phosphorus tribromide and 5 ml of chloroform under ice-cooled condition, then the mixture was stirred under ice-cooled condition for 2 hours, next was stirred at room temperature overnight. To the reaction mixture was added 5%-sodium hydroxide aqueous solution, then was extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain 1.80 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline.

Workup

  1. additionwas added dropwise a solution
  2. temperaturecooled condition
  3. temperaturecooled condition for 2 hours
  4. stirringnext was stirred at room temperature overnight
  5. extractionwas extracted with chloroform
  6. washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ba5ce626a49346099c909ad07942421c
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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