Water → 1-Methyl-4-nitro-1H-indole

HRID 1059836Notes

Reaction equation

HRID 1059836 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-d985eeea41a9442faf9de2aa1fb17777
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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