Ammonia → HCID 19988653, compound

HRID 973547Notes

Reaction equation

HRID 973547 reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][N:13]=2)[CH:7]=1)#[N:5].[Cl-:20].[NH4+:21].[NH3:22]>CO.C(O)(=O)C>[ClH:20].[ClH:20].[C:18]([C:16]1[CH:15]=[CH:14][N:13]=[C:12]([C:8]2[CH:7]=[C:6]([C:4](=[NH:22])[NH2:5])[CH:11]=[CH:10][N:9]=2)[CH:17]=1)(=[NH:21])[NH2:19]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 104429584,4'-DICYANO-2,2'-BIPYRIDINEHCID 10942334Sodium Methoxide

Product 1

HCID 19988653HCID 19988653, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

0.5 ml of 1.1N sodium methoxide in absolute methanol is added to a suspension of 1.2 g (0.0058 mol) of 4,4'-dicyano-2,2'-bipyridine in 48 ml of absolute methanol and the whole is boiled for 5 hours under reflux. 0.05 ml of glacial acetic acid, 0.72 g (0.0134 mol) of ammonium chloride and 10 ml of 4.6N methanolic ammonia solution are then added to the solution while it is still warm and the whole is boiled for a further one hour. The cooled reaction mixture is concentrated by evaporation, taken up in 60 ml of 0.1N hydrochloric acid, filtered and applied to a column of 250 ml of Amberlite® ER 180 adsorber resin. Washing is effected with distilled water and 5 ml fractions are collected. Fractions 14-21 are combined and concentrated by evaporation and the residue is crystallised from a small amount of water to give the title compound; m.p. >280°.

Workup

  1. temperatureunder reflux
  2. temperatureis still warm
  3. waitthe whole is boiled for a further one hour
  4. customThe cooled reaction mixture
  5. concentrationis concentrated by evaporation
  6. filtrationfiltered
  7. washWashing
  8. customare collected
  9. concentrationconcentrated by evaporation
  10. customthe residue is crystallised from a small amount of water

Sources & evidence

ORD record
ord-5677c9ce10ef45b39810d5885288f3e4
Source dataset
uspto-grants-1991_11
Patent number
US05064832

Reaction notes

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