HCID 12979373, compound → 3,7-Dimethyl-1H-indole-2-carbaldehyde

HRID 1362428Notes

Reaction equation

HRID 1362428 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:12][OH:13]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH:12]=[O:13]

Participants

4

Reactant 1

HCID 12979373HCID 12979373, compound

Product 1

HCID 177509263,7-Dimethyl-1H-indole-2-carbaldehydeYield 46.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3,7-dimethyl-1H-indol-2-yl)methanol (440 mg, 2.5 mmol) and manganese dioxide (1.09 g, 12.5 mmol) in dichloromethane (15 mL) was stirred overnight at rt. The mixture was filtered and evaporated. The crude was chromatographed over silica gel eluting with ethyl acetate/hexane (5% and 7.5%) to afford the title compound (200 mg, 46%). 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 8.75 (s, 1H), 7.51 (d, J=7.2 Hz, 1H), 7.15 (d, J=7.4 Hz, 1H), 7.05 (t, J=7.3 Hz, 1H), 2.61 (s, 3H), 2.45 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customThe crude was chromatographed over silica gel eluting with ethyl acetate/hexane (5% and 7.5%)

Sources & evidence

ORD record
ord-19ce02ad86e84093a10d65d6e56f850d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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