Potassium Cyanide → HCID 58504220, compound

HRID 2407741Notes

Reaction equation

HRID 2407741 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C-:15]#[N:16].[K+]>CN(C)C=O.O>[NH2:1][C:2]1[N:10]=[C:9]([C:15]#[N:16])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 58504175HCID 58504175, compound

Product 1

HCID 58504220HCID 58504220, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The compound prepared in Example 238 (0.130 g) and potassium cyanide (0.195 g) were combined in N,N-dimethylformamide (3 mL) and water (0.5 mL) was added. The reaction mixture was heated at 90° C. for 3 hours. The mixture was diluted with water and extracted with ethyl acetate. The aqueous layer was cautiously acidified with 1N hydrochloric acid to pH 1 to 2. It was then extracted with ethyl acetate. These extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated to obtain the title compound (0.105 g) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionIt was then extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d1318c9a2d464e9eaafcd1ba7eb1c08d
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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