Tetramethylammonium → Pyridine, 2,3,5-trichloro-

HRID 128055

Reaction equation

HRID 128055 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6](Cl)[C:5]([Cl:10])=[CH:4][N:3]=1.C[N+](C)(C)C.COP(C)(=O)O>P(OC)(OC)(OC)=O.[Zn]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6380TetramethylammoniumHCID 760512,3,4,5-TetrachloropyridineHCID 316552Monomethyl methylphosphonate

Product 1

HCID 27666Pyridine, 2,3,5-trichloro-Yield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10541Trimethyl PhosphateSolvent

Procedure

By the method described in Example 1, 11.0 g (0.05 mol) of 2,3,4,5-tetrachloropyridine, 4.4 g (0.065 gram atom) of zinc dust (96.5%) and 24.7 g (0.135 mol) of the tetramethylammonium salt of methanephosphonic acid monomethyl ester in 90 ml of trimethyl phosphate are reacted to obtain 7.1 g (78% of theory) of 2,3,5-trichloropyridine, m.p. 47°-47.5° C., which contains, according to gas-chromatographical analysis, 97.6% of 2,3,5-trichloropyridine, 0.4% of 2,3,4,5-tetrachloropyridine and 1.4% of unknown products.

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-cb6cf263b5cc457780a0386174dd4ae1
Source dataset
uspto-grants-1981_03
Patent number
US04258194

Linked notes

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