Acetic Anhydride → 5,6,7,8-Tetrahydroquinolin-8-yl acetate

HRID 2301140Notes

Reaction equation

HRID 2301140 reaction equation
[N+:1]1([O-])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 27781345,6,7,8-Tetrahydro-1-quinoliniumolate

Product 1

HCID 122262495,6,7,8-Tetrahydroquinolin-8-yl acetateYield 33%

Conditions

Temperature
90 °C

Procedure

5,6,7,8-Tetrahydroquinoline N-oxide (1.6 g, 11 mmol) was mixed with acetic anhydride (9.2 ml) and stirred at 90° C. for 7 hours. After removing the solvent by evaporation under a reduced pressure, the residue was neutralized with sodium hydroxide aqueous solution (1 N) and the reaction product was extracted with chloroform. The extract was washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 690 mg (3.6 mmol, 33%) of the title compound.

Workup

  1. customAfter removing the solvent
  2. customby evaporation under a reduced pressure
  3. extractionthe reaction product was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. customthe thus obtained material was separated
  8. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-63fbf13115b54df1b80ed99559a6b0e5
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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