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 1384836Notes

Reaction equation

HRID 1384836 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-carboxaldehydeYield 87.9%

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 hours at reflux. The mixture is cooled and filtered through a Teflon® membrane, the solid is rinsed with dichloromethane and then the filtrate is concentrated under reduced pressure. 2:88 g (8.53 mmol) of compound are isolated in the form of a white solid which is used as is in the following stage.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture is cooled
  3. filtrationfiltered through a Teflon® membrane
  4. washthe solid is rinsed with dichloromethane
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb62aa34eaff4ed0a317470191b64e71
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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