4-Amino-3,5-dinitropyridine → Pyridine-3,4,5-triamine
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]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- customThe flask was evacuated
- custompurged with a nitrogen atmosphere