Sodium Hydroxide → 4-Allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 1638580Notes

Reaction equation

HRID 1638580 reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10](O)[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:16])[CH:2]=[CH2:3].P(Br)(Br)[Br:18].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([Br:18])[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 141555224-Allyloxy-8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 141555234-Allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3.5 Grams of 4-allyloxy-8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline was dissolved in 40 ml of chloroform, to this solution was added dropwise a solution consisting of 2.8 g of phosphorus tribromide and 5 ml of chloroform under ice-cooled condition. The reaction mixture was stirred under ice-cooled condition for 2 hours, further stirred at room temperature for 2 hours. The reaction mixture was poured into a cold sodium hydroxide aqueous solution, then extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. Chloroform was removed by evaporation, then the residue thus obtained was purified by a silica gel column chromatography (eluent: methylene chloride/methanol=100/1) to obtain 1.3 g of 4-allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline.

Workup

  1. additionwas added dropwise a solution
  2. temperaturecooled condition
  3. temperaturecooled condition for 2 hours
  4. stirringfurther stirred at room temperature for 2 hours
  5. extractionextracted 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. customChloroform was removed by evaporation
  9. customthe residue thus obtained
  10. customwas purified by a silica gel column chromatography (eluent: methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-90d50e5fc67d46beaa80731d4786d0ad
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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