Diethylene Glycol → 3-Methyl-5,6,7,8-tetrahydroquinoline

HRID 1973666Notes

Reaction equation

HRID 1973666 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=O)[C:10]=2[CH:11]=1.O.NN.C(O)COCCO.[OH-].[Na+]>O>[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

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 5951923-Methyl-7,8-dihydroquinolin-5(6H)-one

Product 1

HCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-methyl-7,8-dihydro-5(6H)-quinolone (20 g.), hydrazine hydrate (14 ml), diethylene glycol (150 ml.) and sodium hydroxide (14 g) was heated at reflux with stirring for 1 hour. The condenser was replaced by a Dean and Stark Water Separator and the heating continued for a further 3 hours. The cooled reaction mixture was diluted with water (200 ml.) and extracted with ether (3 × 150 ml.). The combined extracts were dried (MgSO4) and the solvent removed in vacuo and the residual oil distilled at 15 mm Hg to give the title compound as a colourless oil b.p. 116° (17 g, 93%) G.L.C. (3% SE30, T=150°) RF = 3.5 min.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. waitthe heating continued for a further 3 hours
  4. customThe cooled reaction mixture
  5. extractionextracted with ether (3 × 150 ml.)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. distillationthe residual oil distilled at 15 mm Hg

Sources & evidence

ORD record
ord-6bdb7d9369af47389585c8dad335baf0
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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