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

HRID 24336Notes

Reaction equation

HRID 24336 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-18414c51c913465db3068c28288db0ef
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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