[3-(3-dimethylaminopropyl)-1H-indol-2-yl]methanol → 3-(3-dimethylaminopropyl)-1H-indole-2-carbaldehyde

HRID 1860736Notes

Reaction equation

HRID 1860736 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:15][OH:16]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:17][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 22571134[3-(3-dimethylaminopropyl)-1H-indol-2-yl]methanol

Product 1

HCID 225710543-(3-dimethylaminopropyl)-1H-indole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (10 equiv.) was added to a solution of [3-(3-dimethylaminopropyl)-1H-indol-2-yl]methanol (2.2 g) in DCM. The mixture was stirred at room temperature for 18 hr. Insoluble materials were removed by filtration and the filtrate was concentrated. The residue was column chromatographed to give 3-(3-dimethylaminopropyl)-1H-indole-2-carbaldehyde as a cream-colored solid.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customchromatographed

Sources & evidence

ORD record
ord-e4060a99cf014fd9ab11e60195f4623b
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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