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

HRID 1004059Notes

Reaction equation

HRID 1004059 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[CH:12]=[CH: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 187942259-Methoxy4,12-dihydroindolo[2,3-a]quinolizin-4-one

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 24 h. After filtration ard washing of the dioxide with an ethyl acetate/methanol mixture (98/2), and after recrystallization from ethyl acetate, 9-methoxy4,12-dihydroindolo[2,3-a]quinolizin-4-one is obtained.

Workup

  1. temperatureAfter refluxing for 2 h 30
  2. temperaturethe mixture is cooled
  3. temperatureThe medium is refluxed for 24 h
  4. filtrationAfter filtration
  5. washard washing of the dioxide with an ethyl acetate/methanol mixture (98/2)
  6. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0fc6f7e29f6f4d288505c3fde4d2643a
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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