Sodium Hydroxide → 8-Hydroxy-5,6,7,8-tetrahydroquinoline

HRID 481760Notes

Reaction equation

HRID 481760 reaction equation
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=O)C.[OH-].[Na+]>CO.O>[OH:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 122262495,6,7,8-Tetrahydroquinolin-8-yl acetate

Product 1

HCID 118159398-Hydroxy-5,6,7,8-tetrahydroquinolineYield 102.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 10 g of 8-acetoxy-5,6,7,8-tetrahydroquinoline in 30 mL of methanol was added 30 mL of 30% sodium hydroxide in water. The mixture was heated to reflux for 2 min and the methanol was removed in vacuo. The residual organic product was extracted with chloroform. The chloroform extracts were dried over sodium sulfate and evaporation of the solvent gave 8 g of product as an oil, characterized by its NMR.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 min
  3. customthe methanol was removed in vacuo
  4. extractionThe residual organic product was extracted with chloroform
  5. dry with materialThe chloroform extracts were dried over sodium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-0092b06f89b94ed58699b8e316af2ebc
Source dataset
uspto-grants-1998_08
Patent number
US05789587

Reaction notes

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