7-Chloro-1-(hydroxymethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one → 7-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxaldehyde

HRID 1937317Notes

Reaction equation

HRID 1937317 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:15]([CH2:16][OH:17])=[N:14][N:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12](=[O:24])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:15]([CH:16]=[O:17])=[N:14][N:13]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:12](=[O:24])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 154619017-Chloro-1-(hydroxymethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one

Product 1

HCID 154619027-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

5.7 g (65.6 mmol) of manganese dioxide are added to a solution of 3.3 g (9.7 mmol) of 7-chloro-1-(hydroxymethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one in 300 ml of dichloromethane and the reaction mixture is stirred for 24 h under reflux.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-67e3f126e9374c0eaa572f992bf8a6f6
Source dataset
uspto-grants-2002_05
Patent number
US06395729B1

Reaction notes

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