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

HRID 2071601Notes

Reaction equation

HRID 2071601 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-ee5b4520329b4703bb0482176f1da996
Source dataset
uspto-grants-1977_09
Patent number
US04048175

Reaction notes

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