3-Methyl-5,6,7,8-tetrahydroquinolin-8-ol → 3-Methyl-6,7-dihydroquinolin-8(5H)-one

HRID 596452Notes

Reaction equation

HRID 596452 reaction equation
[OH:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:12][C:8]1[CH:9]=[N:10][C:11]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=1

Participants

4

Reactant 1

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

Product 1

HCID 123582233-Methyl-6,7-dihydroquinolin-8(5H)-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

8-Hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline (42.5g) in methylene chloride (21/21) was stirred at room temperature with manganese dioxide (425g) for 16 hours. The manganese dioxide was removed by filtration and washed with methylene chloride. The filtrate was evaporated to dryness under reduced pressure and the residue was distilled to give 5,6-dihydro-3-methyl-7H-quinolin-8-one (30g) b.p. 142°-4° C at 0.5mm.

Workup

  1. customThe manganese dioxide was removed by filtration
  2. washwashed with methylene chloride
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-496536554f194f9db858bfd2e49b8427
Source dataset
uspto-grants-1977_03
Patent number
US04011229

Reaction notes

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