Methanesulfonic Acid → HCID 19012219, compound

HRID 1974019Notes

Reaction equation

HRID 1974019 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.CS(O)(=O)=O.[H][H]>[Pd].C.CO>[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

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 197540694,6-Dimethyl-3,5-dinitropyridin-2-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19012219HCID 19012219, compound

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 887MethanolSolvent

Procedure

A 500 ml Parr Bottle was charged with 2-amino-4,6-dimethyl-3,5-dinitropyridine (21.2 g, 0.10 mole), 200 ml methanol, methanesulfonic acid (19.2 g, 0.20 mole), and 20. g 5% Pd/charcoal catalyst. The mixture was subjected to hydrogenation at ambient temperature with an initial hydrogen pressure of 5.7 psig. When no further uptake of hydrogen was observed, the mixture was filtered free of catalyst under a nitrogen atmosphere, and methanol removed under vacuum. The bismethanesulfonate salt of 2,3,5-triamino-4,6-dimethylpyridine so obtained was purified by slurrying with dry isopropyl alcohol, filtering under nitrogen, and vacuum drying over P2O5 at 80° - 90° C.

Workup

  1. filtrationthe mixture was filtered free of catalyst under a nitrogen atmosphere
  2. custommethanol removed under vacuum

Sources & evidence

ORD record
ord-249859c417384553bdaa621540d9c40a
Source dataset
uspto-grants-1976_12
Patent number
US04000146

Reaction notes

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