9-Methoxy-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one → 9-Methoxy4,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4-one

HRID 1004058Notes

Reaction equation

HRID 1004058 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11]3[CH2:12][CH2:13][N:14]4[C:19]([C:10]=3[NH:9][C:6]2=[CH:7][CH:8]=1)=[CH:18][CH2:17][CH2:16][C:15]4=[O:20]>C1COCC1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11]3[CH2:12][CH2:13][N:14]4[C:19]([C:10]=3[NH:9][C:6]2=[CH:7][CH:8]=1)=[CH:18][CH:17]=[CH:16][C:15]4=[O:20]

Participants

4

Reactant 1

HCID 187942129-Methoxy-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one

Product 1

HCID 187942149-Methoxy4,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4-oneYield 55%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

Activated manganese dioxide (400 mg) is added to a solution of 9-methoxy-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one (150 mg) in THF (5 ml). After refluxing for 2 h 30, the mixture is cooled and activated manganese dioxide (400 mg) is again added. The medium is refluxed for 2 h 30. After filtration and washing of the dioxide with an ethyl acetate/methanol mixture (98/2) and after separation on a preparative plate, 9-methoxy4,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4-one is obtained (55% yield).

Workup

  1. temperatureAfter refluxing for 2 h 30
  2. temperaturethe mixture is cooled
  3. temperatureThe medium is refluxed for 2 h 30
  4. filtrationAfter filtration
  5. washwashing of the dioxide with an ethyl acetate/methanol mixture (98/2)
  6. customafter separation on a preparative plate

Sources & evidence

ORD record
ord-0932e1d7b87e4f7c8c8cdfd7ca196734
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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