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

HRID 1763245Notes

Reaction equation

HRID 1763245 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4](Cl)[N:3]=1.[OH-].[Na+]>[Zn].C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Procedure

To a 5-liter 3-neck flask fitted with a reflux condenser, a heater, thermometer and a stirrer were added 216.9 grams (1.0 mole) of 2,3,5,6-tetrachloropyridine, 500 milliliters of benzene, 1.0 liter of 8N sodium hydroxide and 130.7 grams (2.0 gram atoms) of zinc dust. The pH of the mixture was 14-15 and the mixture was heated and refluxed, with stirring, for 7 hours. After completion of the reaction, the reaction mixture was cooled and filtered. The filter cake was washed with benzene and the benzene wash was combined with the filtrate. Gas-liquid chromatography of the mixture indicated a 2,3,5-trichloropyridine content of about 131.35 grams (72 percent of theoretical).

Workup

  1. customTo a 5-liter 3-neck flask fitted with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperaturerefluxed
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was cooled
  6. filtrationfiltered
  7. washThe filter cake was washed with benzene
  8. washthe benzene wash

Sources & evidence

ORD record
ord-2ab1497643c248ce908a897cd9ec7589
Source dataset
uspto-grants-1978_09
Patent number
US04111938

Reaction notes

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