Ammonium Hydroxide → Pyridine, 2,3,5-trichloro-

HRID 1763242Notes

Reaction equation

HRID 1763242 reaction equation
[OH-].[NH4+].Cl[C:4]1[N:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[C:6](Cl)[C:5]=1[Cl:13]>[Zn].C1(C)C=CC=CC=1>[Cl:10][C:8]1[C:7]([Cl:11])=[CH:6][C:5]([Cl:13])=[CH:4][N:9]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 16584Pentachloropyridine

Product 1

HCID 27666Pyridine, 2,3,5-trichloro-

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a 500 milliliter, 3-neck flask which was fitted with a reflux condenser, heater, thermometer and stirrer was added 200 milliliters (1.2 moles) of 6N ammonium hydroxide, 39.0 grams (0.60 gram atom) of zinc dust, 100 milliliters of toluene and 25.1 grams (0.1 mole) of pentachloropyridine. The pH of the mixture was 12.6. The mixture was heated to 70° C., with stirring, and held under these conditions for 35 hours. At the end of this period, the reaction mixture was cooled to 20° C. and filtered to remove insolubles. The filter cake was washed with toluene and the toluene combined with the filtrate and concentrated by distillation. Analysis indicated a 2,3,5-trichloropyridine yield of 9.39 grams (52 percent of theoretical).

Workup

  1. customTo a 500 milliliter, 3-neck flask which was fitted with a reflux condenser
  2. temperatureAt the end of this period, the reaction mixture was cooled to 20° C.
  3. filtrationfiltered
  4. customto remove insolubles
  5. washThe filter cake was washed with toluene
  6. concentrationconcentrated by distillation

Sources & evidence

ORD record
ord-20db836199264b13a3a6123bbc638d06
Source dataset
uspto-grants-1978_09
Patent number
US04111938

Reaction notes

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