Water → 5-methoxy-1-methyl-1H-indole-3-carbaldehyde

HRID 1765586Notes

Reaction equation

HRID 1765586 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]=[O:13].[H-].[Na+].[CH3:16]I.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:16])[CH:7]=[C:6]2[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 827585-Methoxyindole-3-carbaldehyde

Product 1

HCID 9259735-methoxy-1-methyl-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methoxyindole-3-carboxaldehyde (80 g) in dimethylformamide (1L) under nitrogen was treated portion-wise with sodium hydride (20.1 g, 60% dispersion in mineral oil) over 15 minutes. After stirring at ambient temperature for 30 minutes the mixture was treated dropwise with methyl iodide (31.3 mL) over 10 minutes and stirring was then continued for a further 2 hours. The reaction mixture was poured cautiously into water then extracted with ethyl acetate. The organic phase was washed with water, then dried over sodium sulfate and then evaporated. The residue was triturated with pentane to give the title compound (76 g) as a pale brown solid, m.p. 133–134° C. 1H NMR [(CD3)2SO]: δ 9.86 (1H, s); 8.20 (1H, s); 7.60 (1H, d, J=2.6 Hz); 7.50 (1H, d, J=8.9 Hz); 6.96 (1H, dd, J=8.9 and 2.6 Hz); 3.86 and 3.80 (6H, s).

Workup

  1. stirringstirring
  2. waitwas then continued for a further 2 hours
  3. extractionthen extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-628808dc7be44464bce1d3f38216376a
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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