Sodium Hydroxide → 3-Methyl-5,6,7,8-tetrahydroquinolin-8-ol

HRID 596446Notes

Reaction equation

HRID 596446 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.[OH-:13].[Na+]>C(OC(=O)C)(=O)C>[OH:13][CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 123582463-Methyl-1-oxo-5,6,7,8-tetrahydro-1lambda~5~-quinoline

Product 1

HCID 123582223-Methyl-5,6,7,8-tetrahydroquinolin-8-ol

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

The N-oxide (60 g.) was dissolved in acetic anhydride (120 ml.) and added to boiling acetic anhydride (120 ml.) and the mixture heated at reflux for 30 minutes. The solvent was removed in vacuo and the residual oil was treated with 10% hydrochloric acid (700 ml.) and the solution heated on a steam bath for 2 hours. The cooled reaction mixture was adjusted to pH 9.0 with sodium hydroxide and extracted with ether (3 × 100 ml). The combined ethereal extracts were washed with saturated brine, dried (MgSO4) and the solvent removed in vacuo. The resultant oil as distilled at 0.15 mmHg to give a colourless oil (22 g.) b.p. 70°-78° C which crystallised from n-hexane to give 8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline as colourless needles m.p. 58° C.

Workup

  1. additionadded
  2. temperaturethe mixture heated
  3. temperatureat reflux for 30 minutes
  4. customThe solvent was removed in vacuo
  5. additionthe residual oil was treated with 10% hydrochloric acid (700 ml.)
  6. temperaturethe solution heated on a steam bath for 2 hours
  7. customThe cooled reaction mixture
  8. extractionextracted with ether (3 × 100 ml)
  9. washThe combined ethereal extracts were washed with saturated brine
  10. dry with materialdried (MgSO4)
  11. customthe solvent removed in vacuo
  12. distillationThe resultant oil as distilled at 0.15 mmHg
  13. customto give a colourless oil (22 g.) b.p. 70°-78° C which
  14. customcrystallised from n-hexane

Sources & evidence

ORD record
ord-5781e80167ee4203943db9a2ba8c765f
Source dataset
uspto-grants-1977_03
Patent number
US04011229

Reaction notes

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