Water → 1-Methyl-4-nitro-1H-indole

HRID 583925Notes

Reaction equation

HRID 583925 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].[H-].[Na+].[CH3:15]I.O>C1COCC1.C(OCC)(=O)C>[CH3:15][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indole

Product 1

HCID 131680671-Methyl-4-nitro-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitroindole (500 mg, 3.1 mmol) in THF (15 mL) at 0° C. was treated portionwise with NaH (290 mg, 9.3 mmol), stirred for 30 minutes, treated dropwise with methyl iodide (0.95 mL, 15.5 mmol), warmed to room temperature for 18 hours, treated sequentially with water and ethyl acetate (200 mL), and washed with brine (100 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to provide the desired product, which was used in the next step without further purification.

Workup

  1. washwashed with brine (100 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2477409147ff4825b3296cbd8390e49d
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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