2-Hydroxymethyl-1-methyl-4,5,6-trimethoxyindole → 1-Methyl-4,5,6-trimethoxyindole-2-carboaldehyde

HRID 720340Notes

Reaction equation

HRID 720340 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH3:18])[C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:13])[C:8]([O:14][CH3:15])=[C:7]([O:16][CH3:17])[CH:6]=2>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:18][N:4]1[C:5]2[C:10](=[C:9]([O:12][CH3:13])[C:8]([O:14][CH3:15])=[C:7]([O:16][CH3:17])[CH:6]=2)[CH:11]=[C:3]1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 218916442-Hydroxymethyl-1-methyl-4,5,6-trimethoxyindole

Product 1

HCID 218916451-Methyl-4,5,6-trimethoxyindole-2-carboaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

2-Hydroxymethyl-1-methyl-4,5,6-trimethoxyindole (861 mg) was dissolved in benzene (50 mL), activated manganese dioxide (8.7 g) was added to the solution, and the mixture was stirred at room temperature for 2 hours. After the reaction mixture was filtered, and the filtrate was concentrated, the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-bbef7f3f66b74e0b8ce28d675ed35a56
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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