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

HRID 2097176Notes

Reaction equation

HRID 2097176 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-8500ad7e75ef4b818eb62592944e0787
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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