Hydrochloric Acid → HCID 19012219, compound

HRID 2397587Notes

Reaction equation

HRID 2397587 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[C:5]([N+:12]([O-])=O)=[C:4]([CH3:15])[N:3]=1.C(O)C.[H][H].Cl>[Pd].C.C(O)(C)C>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:11])[C:5]([NH2:12])=[C:4]([CH3:15])[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 197540694,6-Dimethyl-3,5-dinitropyridin-2-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19012219HCID 19012219, compound

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 3776IsopropanolSolvent

Procedure

A 500 ml Parr Bottle was charged with 2-amino-4,6-dimethyl-3,5-dinitropyridine (21.2 g, 0.10 mole), 250 ml absolute ethanol, and 20 g 5% Pd/charcoal catalyst. The mixture was subjected to hydrogenation at ambient temperature with an initial hydrogen pressure of 60 psig. When no further uptake of hydrogen was observed, the mixture was filtered free of catalyst under a nitrogen atmosphere, and concentrated under vacuum to a volume of about 100 ml. The product concentrate was treated, under nitrogen at ice temperature, with a cold solution of hydrogen chloride (0.5 mole) in 85 ml anhydrous isopropyl alcohol. The trihydrochloride salt of 2,3,5-triamino-4,6-dimethylpyridine was obtained after vigorous stirring, filtering under nitrogen, and vacuum drying under high vacuum over P2O5 at 80°-90° C.

Workup

  1. filtrationthe mixture was filtered free of catalyst under a nitrogen atmosphere
  2. concentrationconcentrated under vacuum to a volume of about 100 ml
  3. concentrationThe product concentrate

Sources & evidence

ORD record
ord-2a56b0bd65d64252a834100e2697cee7
Source dataset
uspto-grants-1977_05
Patent number
US04022793

Reaction notes

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