6-Hydroxymethylindole → 1H-Indole-6-carboxaldehyde

HRID 330152

Reaction equation

HRID 330152 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 27734596-Hydroxymethylindole

Product 1

HCID 27734351H-Indole-6-carboxaldehydeYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (240 g) was added to a mechanically stirred solution of 6-hydroxymethylindole (40.7 g) in methylene chloride (1.6 liter). The mixture was stirred for 18 hr, filtered through a pad of diatomaceous earth, the filter cake washed with methylene chloride and chloroform, and the filtrate evaporated to give 6-formylindole (30.55 g) as a yellow solid. The filter cake was washed with tetrahydrofuran and the washings evaporated to give a further crop of 6-formylindole (2.35 g, 82% combined yield); partial NMR (250 MHz, DMSO-d6): 6.58(m, 1H, H3 -indole), 10.00(s, 1H, CHO), 11.71(br s, 1H, NH).

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. washthe filter cake washed with methylene chloride and chloroform
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-27cd4d962190435db17d3ab2c9a33f3b
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Linked notes

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