Potassium Cyanide → 1H-Indole-3-acetonitrile, 4-nitro-

HRID 1696351Notes

Reaction equation

HRID 1696351 reaction equation
[C-:1]#[N:2].[K+].CN(C)[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:16]([O-:18])=[O:17])[NH:9][CH:8]=1>O.CN(C=O)C>[N+:16]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:7]([CH2:6][C:1]#[N:2])=[CH:8][NH:9]2)([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 2514534-NITROGRAMINE

Product 1

HCID 109545951H-Indole-3-acetonitrile, 4-nitro-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium cyanide (9.20 g, 141 mmol) in H2O (80 mL) was added to a solution of N,N-dimethyl-1-(4-nitro-1H-indol-3-yl)methanamine from Step A (3.10 g, 14.1 mmol) in DMF (80 mL) and the mixture was heated at reflux for 1 h, then cooled to ambient temperature and partitioned between H2O (200 mL) and EtOAc (400 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=265 (M+Na+CH3CN).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. custompartitioned between H2O (200 mL) and EtOAc (400 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-c9f3361988104b2a9ae91d3ceb4c6562
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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