Methyl iodide → 2-Chloro-1-methyl-5-nitroindole-3-carbaldehyde

HRID 1957214Notes

Reaction equation

HRID 1957214 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2.[H-].[Na+].[CH3:18]I>C1COCC1>[Cl:1][C:2]1[N:3]([CH3:18])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 38092012-chloro-5-nitro-1H-indole-3-carbaldehyde

Product 1

HCID 108238742-Chloro-1-methyl-5-nitroindole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5 g of (65) in 100 ml THF was added 550 mg NaH and 2.5 ml methyliodide. The reaction was left with stirring overnight. Most of the THF was evaporated off, water was added, and the water phase extracted with EtOAc. The water phase was then acidified with acetic acid, which precipitated the pure product. Filtration and drying gave 770 mg of (66).

Workup

  1. waitThe reaction was left
  2. customMost of the THF was evaporated off
  3. additionwater was added
  4. extractionthe water phase extracted with EtOAc
  5. customprecipitated the pure product
  6. filtrationFiltration
  7. customdrying

Sources & evidence

ORD record
ord-2ac73b4ba323450a8e575613998a422c
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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