4-Amino-3,5-dinitropyridine → Pyridine-3,4,5-triamine

HRID 729352Notes

Reaction equation

HRID 729352 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([N+:11]([O-])=O)[C:9]=1[NH2:10])([O-])=O>CCO>[N:6]1[CH:7]=[C:8]([NH2:11])[C:9]([NH2:10])=[C:4]([NH2:1])[CH:5]=1

Participants

3

Reactant 1

HCID 2713234-Amino-3,5-dinitropyridine

Product 1

HCID 419566Pyridine-3,4,5-triamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Dinitro-pyridin-4-ylamine 2 (5.00 g, 27 mmol) was suspended in EtOH (80 ml). The flask was evacuated and then purged with a nitrogen atmosphere. To this flask, Pt/C (500 mg of 10%) was added. The flask was re-evacuated, and then placed under a hydrogen atmosphere (40 psi) on a Parr hydrogenator. It was allowed to shake for 18 hours, and was judged complete by TLC. The platinum catalyst was removed by CELITE filtration, and the solvent was removed by evaporation under a reduced atmosphere to yield the title product 3, a brown solid (3.24 g (97%), 27 mmol). 1H NMR (20): δ 7.51 (s, 2H). MS (ESI-POS): [M+H]+=125.

Workup

  1. customThe flask was evacuated
  2. custompurged with a nitrogen atmosphere
  3. additionTo this flask, Pt/C (500 mg of 10%) was added
  4. customThe flask was re-evacuated
  5. customThe platinum catalyst was removed by CELITE filtration
  6. customthe solvent was removed by evaporation under a reduced atmosphere

Sources & evidence

ORD record
ord-c93441afe0d644aabaf5f7f965d4d73a
Source dataset
uspto-grants-2009_09
Patent number
US07582634B2

Reaction notes

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