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

HRID 73927Notes

Reaction equation

HRID 73927 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-d32efaff395247b0a1519669f91eb7fb
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

Loading…