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

HRID 1638579Notes

Reaction equation

HRID 1638579 reaction equation
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][C:11]([CH3:15])=[C:10]([O:16][CH2:17][CH:18]=[CH2:19])[C:9]=2[CH2:8][CH2:7][CH2:6]1)(=O)C.[OH-].[Na+]>CO.O>[CH2:17]([O:16][C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:4])[C:14]=2[N:13]=[CH:12][C:11]=1[CH3:15])[CH:18]=[CH2:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 141555218-Acetoxy-4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 141555224-Allyloxy-8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

5.0 Grams of 8-acetoxy-4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline was dissolved in 20 ml of methanol. Then a solution prepared by dissolving 2.3 g of sodium hydroxide in 20 ml of water was added thereto, and the mixture was refluxed for 1 hour. After the reaction was completed, methanol was removed by evaporation, and to the residue thus obtained was added water, and was 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 to obtain 3.5 g of 4-allyloxy-8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline in the form of brown oily substance.

Workup

  1. customThen a solution prepared
  2. additionwas added
  3. temperaturethe mixture was refluxed for 1 hour
  4. custommethanol was removed by evaporation
  5. customto the residue thus obtained
  6. extractionwas extracted with chloroform
  7. washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customChloroform was removed by evaporation

Sources & evidence

ORD record
ord-af09636588be459799b7216d48b2cb6d
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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