Potassium Cyanide → HCID 13959015, compound

HRID 255863Notes

Reaction equation

HRID 255863 reaction equation
[C-:1]#[N:2].[K+].C1(C)C=CC(S([C:13]2[C:22]3[C:17](=[C:18]([CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=3)[N:16]=[N:15][CH:14]=2)(=O)=O)=CC=1>CN(C=O)C>[C:1]([C:13]1[C:22]2[C:17](=[C:18]([CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=2)[N:16]=[N:15][CH:14]=1)#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium Cyanide2×HCID 20164597HCID 20164597, compound

Product 1

HCID 13959015HCID 13959015, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of potassium cyanide was added to a stirred solution of 4.4 g of 53F in 60 ml of dry DMF at room temperature, under nitrogen. The mixture was stirred overnight at room temperature, under nitrogen, then 200 mg potassium cyanide was added and the mixture was stirred for 5 hours at room temperature. The mixture was quenched in water and filtered. The solid was dissolved in ethyl acetate, the solution was washed with water, dried (MgSO4), filtered and stripped of solvent, to give 4-cyano-8-ethylcinnoline (53G), as a yellow solid, m.p.: 102°-104° C., with decomposition.

Workup

  1. stirringthe mixture was stirred for 5 hours at room temperature
  2. customThe mixture was quenched in water
  3. filtrationfiltered
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9ac19efdb29f4c159369fd3b286d41a9
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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