2-Amino-3,5-dinitropyridine → Pyridine-2,3,5-triamine

HRID 564001Notes

Reaction equation

HRID 564001 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1>CO.C1COCC1.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([NH2:11])=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 5043402-Amino-3,5-dinitropyridine

Product 1

HCID 14626209Pyridine-2,3,5-triamineYield 98.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5 g 2-Amino-3,5-dinitropyridine in a mixture of 66 ml methanol and 33 ml THF were hydrogenated over 800 mg 10% palladium on charcoal at room temperature and atmospheric pressure. After the calculated amount of hydrogen was consumed, the catalyst was filtered off and the filtrate was concentrated under vacuum yielding 3.31 g of the crude product which was used for the next step without further purification.

Workup

  1. customAfter the calculated amount of hydrogen was consumed
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-6e29d33d1009406391acf6a39d00ad7a
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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