Water → 1,6-Dimethyl-1H-indole-3-carbaldehyde

HRID 442744Notes

Reaction equation

HRID 442744 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[CH3:15][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)[C:6]([CH:11]=[O:12])=[CH:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 47779026-Methylindole-3-carboxaldehyde

Product 1

HCID 225937461,6-Dimethyl-1H-indole-3-carbaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the known 6-methyl-1H-indole-3-carboxaldehyde (5 g, 31 mm) in DMF (100 mL) was cooled to 0° C. and treated with NaH (38 mm), and stirred at 0° C. for 3 hours. After treatment with CH3I (2.35 mL, 38 mm), the mixture was allowed to warm to room temperature overnight. The mixture was poured into H2O(500 mL) and extracted with ethylacetate (EtOAc) (200 mL×3). The combined organic layers were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.2 g, 97%).

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionextracted with ethylacetate (EtOAc) (200 mL×3)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-56cb28cf919340c083e1a725acc2a2fc
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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