Hydrazine → 2,3,5,6-Tetrachloropyridine

HRID 129546Notes

Reaction equation

HRID 129546 reaction equation
ClC1C(Cl)=CC=C(Cl)N=1.ClC1C=CC=C(Cl)N=1.[Cl:18][C:19]1[N:24]=[C:23]([Cl:25])[C:22]([Cl:26])=[C:21](Cl)[C:20]=1[Cl:28].NN.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(O)C.C(N(CC)CC)C.[OH-].[Na+]>[Cl:25][C:23]1[C:22]([Cl:26])=[CH:21][C:20]([Cl:28])=[C:19]([Cl:18])[N:24]=1

Participants

8

Reactant 5

HCID 9321HydrazineHCID 16584Pentachloropyridine2×HCID 169892,6-DichloropyridineHCID 230162,3,6-TrichloropyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 169902,3,5,6-Tetrachloropyridine

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 22663003EtOH triethylamineSolvent

Procedure

2,3,6-Trichloropyridine is obtained, for example, in the chlorination of 2,6-dichloropyridine (EP Patent 239,904), in the treatment of pentachloropyridine with hydrazine in ethanol/triethylamine and sodium hydroxide solution (U.S. Pat. No. 3,947,457), and selectively in the reduction of pentachloropyridine with lithium aluminum hydride (F. Binns, S.M. Roberts, H. Suschitzky, J. Chem. Soc. C, (1970) (10), 1375-1380; J. Chem. Soc. D (1969) (20), 1211-1212). 2,3,5,6-Tetrachloropyridine can also be obtained in this way if less reductant is employed.

Sources & evidence

ORD record
ord-5f39220aa04c43c5b212c26e61f4b5d1
Source dataset
uspto-grants-1995_11
Patent number
US05468863

Reaction notes

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