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

HRID 1763244Notes

Reaction equation

HRID 1763244 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[C:4](Cl)[C:3]=1[Cl:11].[OH-].[Na+]>[Zn].C1C=CC=CC=1>[Cl:8][C:6]1[C:5]([Cl:9])=[CH:4][C:3]([Cl:11])=[CH:2][N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 16584Pentachloropyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

Into a 5-liter fluted 3-neck flask fitted with a reflux condenser, a heater, thermometer and a stirrer was added 251.0 grams (1.0 mole) of pentachloropyridine, 500 milliliters of benzene and 1.25 liters of 8N sodium hydroxide (10 moles). The mixture was heated to ~75° C., with stirring. At this time, 260.0 grams (4.0 gram atoms) of zinc dust was added and the mixture refluxed at ~79° C. for a total reaction time of 5 hours. The pH of the reaction mixture was 14-15. At the completion of the reaction, the reaction mixture was cooled to room temperature and filtered to remove insolubles. The filter cake was washed with benzene and the benzene wash was combined with the filtrate. Gas-liquid chromatography indicated a 2,3,5-trichloropyridine content of 140.9 grams (77 percent of theoretical).

Workup

  1. customfitted with a reflux condenser
  2. temperatureThe mixture was heated to ~75° C.
  3. temperaturethe mixture refluxed at ~79° C. for a total reaction time of 5 hours
  4. customAt the completion of the reaction
  5. filtrationfiltered
  6. customto remove insolubles
  7. washThe filter cake was washed with benzene
  8. washthe benzene wash

Sources & evidence

ORD record
ord-a996a9041f88426a95c39d4f7869ccae
Source dataset
uspto-grants-1978_09
Patent number
US04111938

Reaction notes

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