Dimethylformamide → 1h-Indole-3-acetonitrile, 6-nitro-

HRID 2189544Notes

Reaction equation

HRID 2189544 reaction equation
[CH3:1][N:2](C=O)C.CI.CN(C)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[C-]#N.[K+]>O.C1COCC1>[N+:20]([C:16]1[CH:15]=[C:14]2[C:19]([C:11]([CH2:10][C:1]#[N:2])=[CH:12][NH:13]2)=[CH:18][CH:17]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 233856-Nitrogramine

Product 1

HCID 2523851h-Indole-3-acetonitrile, 6-nitro-Yield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of DMF (35 mL) and MeI (74.6 g, 0.53 mol) in water (35 mL) and THF (400 mL) was added dimethyl-(6-nitro-1H-indol-3-ylmethyl)-amine (23 g, 0.105 mol). After the reaction mixture was refluxed for 10 min, potassium cyanide (54.6 g, 0.84 mol) was added and the mixture was kept refluxing overnight. The mixture was then cooled to room temperature and filtered. The filtrate was washed with brine (300 mL×3), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give (6-nitro-1H-indol-3-yl)-acetonitrile (B-9-a) (7.5 g, 36%).

Workup

  1. temperatureAfter the reaction mixture was refluxed for 10 min
  2. temperaturethe mixture was kept refluxing overnight
  3. filtrationfiltered
  4. washThe filtrate was washed with brine (300 mL×3)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c5830e183714b8da3d07ae7534f9ae0
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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