Acetic Anhydride → 3-Methyl-8-acetoxy-5,6,7,8-tetrahydroquinoline

HRID 649174Notes

Reaction equation

HRID 649174 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:16][C:13](=[O:15])[CH3:14])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 123582463-Methyl-1-oxo-5,6,7,8-tetrahydro-1lambda~5~-quinoline

Product 1

HCID 123582473-Methyl-8-acetoxy-5,6,7,8-tetrahydroquinoline

Conditions

Temperature
90 °C

Procedure

7.02 Grams of 3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide was dissolved in acetic anhydride, and the solution was heated at 90° C. with stirring for 3.5 hours. Acetic anhydride was removed by evaporation under reduced pressure, then an aqueous solution of sodium carbonate was added to make the residue alkaline and was extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue thus obtained was purified by a silica gel column chromatography (eluent: dichloromethane) to obtain 7.18 g of 3-methyl-8-acetoxy-5,6,7,8-tetrahydroquinoline.

Workup

  1. customAcetic anhydride was removed by evaporation under reduced pressure
  2. additionan aqueous solution of sodium carbonate was added
  3. extractionwas extracted with chloroform
  4. washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue thus obtained
  8. customwas purified by a silica gel column chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-9ff5ea80dbe241509b5a913619dcb36e
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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