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

HRID 549036

Reaction equation

HRID 549036 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 (1 L) 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-f00a90e482cc4965af789de1afe75896
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Linked notes

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