Potassium Iodide → HCID 89656291, compound

HRID 2206862Notes

Reaction equation

HRID 2206862 reaction equation
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)\[C:4]#[N:5].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19]Br)[N:14]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[Br:12][C:13]1[N:14]=[C:15]([CH2:19][O:1]/[N:2]=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)\[C:4]#[N:5])[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 5464219N-Hydroxybenzimidoyl cyanideHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 89656291HCID 89656291, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (6.0 g, 41.1 mmol, 1 eq.) in 80 ml of acetonitrile and 10 ml of DMF, was added 2-bromo-6-(bromomethyl)pyridine (10.3 g, 41.1 mmol, 1.0 eq.) followed by potassium iodide (681 mg, 4.11 mmol, 0.1 eq.) and caesium carbonate (20.1 g, 61.1 mmol, 1.5 eq.). The reaction was stirred 4 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. After separation, the organic phase was dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(6-bromopyridin-2-yl)methoxy]imino}(phenyl)acetonitrile (11.3 g, 86% yield) as a white solid.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washsubsequently washed with H2O and brine
  4. customAfter separation
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8e746cabfcd04a9c8d420d34a94233d6
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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