Water → (1-Methyl-6-nitro-1H-indol-3-yl)-acetonitrile

HRID 1004208Notes

Reaction equation

HRID 1004208 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:19][C:20]#[N:21])=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH3:22]I.O>CN(C)C=O>[CH3:22][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([N+:7]([O-:9])=[O:8])[CH:18]=2)[C:14]([CH2:19][C:20]#[N:21])=[CH:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2523851h-Indole-3-acetonitrile, 6-nitro-

Product 1

HCID 21999030(1-Methyl-6-nitro-1H-indol-3-yl)-acetonitrileYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

65.5 g (0.474 mol) of powdered potassium carbonate was added to a solution of 28.9 g (0.143 mol) of (6-nitro-1H-indol-3,yl)-acetonitrile (13) from Step C above in 230 ml of dimethylformamide at room temperature. The suspension was stirred for 40 minutes then 25.48 g (0.179 mol) of methyl iodide was added dropwise over 65 minutes. After stirring at room temperature over night the reaction mixture was cooled and poured into a total of 600 ml of water. The precipitate was filtered, washed with a little water and dried on phosphor anhydride until reaching constant weight. The procedure yielded 30.4 g (95.4%) of (1-methyl-6-nitro-1H-indol-3-yl)acetonitrile (14), which was used without further purification.

Workup

  1. stirringAfter stirring at room temperature over night the reaction mixture
  2. temperaturewas cooled
  3. filtrationThe precipitate was filtered
  4. washwashed with a little water
  5. dry with materialdried on phosphor anhydride

Sources & evidence

ORD record
ord-9b1f4588515e487bb45d15caee771637
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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