Dimethylamine → N,N-Dimethyl-2,6-pyridinediamine

HRID 1154693Notes

Reaction equation

HRID 1154693 reaction equation
C[NH:2]C.BrC[C:6]1[N:11]=[C:10]([N:12]2[C:16](=O)C3=CC=CC=C3[C:13]2=O)[CH:9]=[CH:8][CH:7]=1>C(O)C>[CH3:13][N:12]([CH3:16])[C:10]1[N:11]=[C:6]([NH2:2])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dione

Product 1

HCID 22287845N,N-Dimethyl-2,6-pyridinediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (140 ml) saturated with dimethylamine gas at ice bath temperature is added 6-bromomethyl-2-phthalimido-pyridine (13.6 gm, 43 mmol). After stirring for 2 hours, the solution is concentrated to half volume to remove any excess dimethylamine. Hydrazine hydrate (2.4 ml) is added and refluxed for 2 hours. The reaction is cooled, filtered to remove precipitated byproduct and evaporated to dryness. The residue is dissolved in chloroform, washed with water, dried over anhydrous sodium sulfate, filtered and evaporated to give 3.8 gm of 6-dimethylamino-2-amino pyridine as an oil.

Workup

  1. concentrationthe solution is concentrated to half volume
  2. customto remove any excess dimethylamine
  3. additionHydrazine hydrate (2.4 ml) is added
  4. temperaturerefluxed for 2 hours
  5. temperatureThe reaction is cooled
  6. filtrationfiltered
  7. customto remove
  8. customprecipitated byproduct
  9. customevaporated to dryness
  10. dissolutionThe residue is dissolved in chloroform
  11. washwashed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customevaporated

Sources & evidence

ORD record
ord-5fd98d325ed84c13ad3377d6a5aa6cdd
Source dataset
uspto-grants-1984_12
Patent number
US04490533

Reaction notes

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