Sodium Hydroxide → 2,3,6-Trichloropyridine

HRID 918452Notes

Reaction equation

HRID 918452 reaction equation
O.NN.[OH-].[Na+].[Cl:6][C:7]1[N:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[C:9](Cl)[C:8]=1Cl>O>[Cl:13][C:11]1[C:10]([Cl:14])=[CH:9][CH:8]=[C:7]([Cl:6])[N:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16584PentachloropyridineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 230162,3,6-Trichloropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Collins et al., J. Chem. Soc., (c); pages 167-174 (1971) teach that halogens ortho and para to the ring nitrogen in pentachloropyridine are reactive with hydrazine hydrate. This reference further teaches the formation of tetrahalo-4-hydroxy pyridine from the action of aqueous sodium hydroxide on tetrahalo-4-hydrazino pyridines. From this same starting material, 2,3,6-trichloropyridine is formed from the reaction with cuprous oxide in hot water.

Sources & evidence

ORD record
ord-68f3d21a828840e3aed137419e40e2b9
Source dataset
uspto-grants-1976_07
Patent number
US03971799

Reaction notes

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