2-Chloro-3,5-dinitropyridine → 2-Chloropyridine-3,5-diamine

HRID 1378431Notes

Reaction equation

HRID 1378431 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1.[H][H]>CCOC(C)=O>[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([NH2:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 757382-Chloro-3,5-dinitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 221212822-Chloropyridine-3,5-diamineYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A tablespoonful of Raney nickel catalyst in water was washed first with 95% EtOH and then with EtOAc; it was added to a solution of 2-chloro-3,5-dinitropyridine (4.00 g, 0.0196 mol) in EtOAc (150 ml) and the mixture was hydrogenated at an initial hydrogen pressure of 47.5 p.s.i. for 3 hours. The mixture was filtered through celite and the filtrate was concentrated. The residue was crystallized from CH2Cl2 -pentane to give 1.83 g of the titled product.

Workup

  1. washA tablespoonful of Raney nickel catalyst in water was washed first with 95% EtOH
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was crystallized from CH2Cl2 -pentane

Sources & evidence

ORD record
ord-245cbdc85ebf433689f42b5463aa961f
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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