Ammonia → 3,5-Dimethylpyridine-2,6-diamine

HRID 661017Notes

Reaction equation

HRID 661017 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]([CH3:9])[C:7]#[N:8])[C:3]#[N:4].[NH3:10]>>[NH2:4][C:3]1[C:2]([CH3:1])=[CH:5][C:6]([CH3:9])=[C:7]([NH2:10])[N:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 226729902,4-Dimethylpentanedinitrile

Product 1

HCID 230493943,5-Dimethylpyridine-2,6-diamine

Conditions

Temperature
200 °C

Procedure

3,5-dimethylglutarimidine is prepared from 2,4-dimethylglutaronitrile using the procedure of Example 2. One equivalent of 3,5-dimethyiglutarimidine is combined with Pd·C catalyst in a Hastelloy shaker tube to which liquid NH3 (59 eq.) is added. The mixture is heated at 200° C. for 45 h. The mixture is cooled to ambient temperature and the excess NH3 removed by N2 purge. The crude mixture is suspended in anhydrous MeOH, the catalyst is removed by syringe filtration, and the crude reaction mixture is concentrated in vacuo. 3,5-dimethylglutarimidine conversion is >90% to give 2,6-diamino-3,5-dimethylpyridine in at least 1% net yield.

Workup

  1. additionis added
  2. temperatureThe mixture is cooled to ambient temperature
  3. customthe excess NH3 removed by N2
  4. custompurge
  5. customthe catalyst is removed by syringe
  6. filtrationfiltration
  7. customthe crude reaction mixture
  8. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-36a4b2fd7f4c479888e3c255122aa8c8
Source dataset
uspto-grants-2011_12
Patent number
US08084569B2

Reaction notes

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