Water → 2-Chloro-1-methyl-1H-indole-3-carbaldehyde

HRID 1678109Notes

Reaction equation

HRID 1678109 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[Cl:1][C:2]1[N:3]([CH3:15])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehydeYield 108.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-1H-indole-3-carboxaldehyde (1.0 g, 5.5 mmol) in DMF (30 mL) is treated portionwise over 10 min with 60% sodium hydride (440 mg, 11 mmol). After stirring for 30 min, methyl iodide (685 μL, 11 mmol) is slowly added and the resulting mixture is stirred 3 hr at room temperature. Water (5 mL) is cautiously added and the solvents are removed. The residue is dissolved in ethyl acetate and washed with water, with brine, dried, filtered and concentrated to give 2-chloro-1-methyl-1H-indole-3-carboxaldehyde (1.16 g, 105%), mp 94.5-95.5° C., as a white solid. MS 194 (M+H).

Workup

  1. stirringthe resulting mixture is stirred 3 hr at room temperature
  2. customthe solvents are removed
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water, with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bd3e615a96d641e18ea81bea2cfc7fd7
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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