Potassium Cyanide → HCID 66989070, compound

HRID 2407764Notes

Reaction equation

HRID 2407764 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH3:13])[N:3]=1.[C-:14]#[N:15].[K+]>CN(C)C=O>[CH2:12]([O:11][C:4]1[N:3]=[C:2]([C:14]#[N:15])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)[CH3:13]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 8172142-bromo-6-ethoxy-3-nitropyridine

Product 1

HCID 66989070HCID 66989070, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound prepared in Example 279 (0.317 g) in N,N-dimethylformamide (6 mL) was added potassium cyanide (0.100 g) at room temperature. The mixture was heated at 80° C. for 18 hours and then cooled to room temperature. The solids were filtered, and the filtrate diluted with ethyl acetate, washed with 1N hydrochloric acid and water. The organic layer was filtered, evaporated in vacuo and purified by column chromatography on silica gel (10-50% ethyl acetate in hexane) to obtain the title compound (0.096 g) having the following physical data.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe solids were filtered
  3. additionthe filtrate diluted with ethyl acetate
  4. washwashed with 1N hydrochloric acid and water
  5. filtrationThe organic layer was filtered
  6. customevaporated in vacuo
  7. custompurified by column chromatography on silica gel (10-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-65af8d9478df47698328469f64d40e7e
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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