Hydrogen Peroxide → 3-Methyl-1-oxo-5,6,7,8-tetrahydro-1lambda~5~-quinoline

HRID 596445Notes

Reaction equation

HRID 596445 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[OH:12]O>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

3-Methyl-5,6,7,8-tetrahydroquinoline (50 g.) was dissolved in glacial acetic acid (180 ml.) and the solution treated with 30% hydrogen peroxide (70 ml.) and heated at 80° C for 20 hours. The solvent was removed in vacuo and the residual oil diluted with water (25 ml.) and re-evaporated. The resulting oil was dissolved in chloroform (100 ml.), washed with aqueous sodium carbonate (2 × 25 ml.), saturated brine (2 × 25 ml.), dried (MgSO4) and the solvent removed in vacuo to give 3-Methyl-5,6,7,8-tetrahydroquinoline-1-oxide (60 g.) as a pale yellow solid which was used without purification.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residual oil diluted with water (25 ml.)
  3. customre-evaporated
  4. dissolutionThe resulting oil was dissolved in chloroform (100 ml.)
  5. washwashed with aqueous sodium carbonate (2 × 25 ml.), saturated brine (2 × 25 ml.)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-746b476fc2664a33841b15201b862c89
Source dataset
uspto-grants-1977_03
Patent number
US04011229

Reaction notes

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