Potassium Cyanide → HCID 131733584, compound

HRID 1749467Notes

Reaction equation

HRID 1749467 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)(=O)=O.[C-:14]#[N:15].[K+].C(=O)(O)[O-].[Na+]>CCO.O>[Cl:13][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([CH2:6][N+:15]#[C-:14])[CH:12]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 118162072HCID 118162072, compound

Product 1

HCID 131733584HCID 131733584, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of (5-chloropyridin-3-yl)methyl methanesulfonate (2.09 g, crude) in EtOH (45 mL) and water (5 mL) was added potassium cyanide (926 mg, 14.3 mmol), and the resulting mixture was stirred at 85° C. for 2 h. Sodium bicarbonate was added and the mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (50% ethyl acetate in petroleum ether) to afford the title compound as a yellow solid (820 mg, 5.43 mmol, 48% yield, 2 steps). MS (ESI) m/z 153.1 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f1fd4691642a488980a9fbbb9ee13cbf
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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