Sodium Hydroxide → Pyridine, 2,3,5-trichloro-
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customTo a 5-liter 3-neck flask fitted with a reflux condenser
- temperaturethe mixture was heated
- temperaturerefluxed
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled
- filtrationfiltered
- washThe filter cake was washed with benzene
- washthe benzene wash
Sources & evidence
- ORD record
- ord-2ab1497643c248ce908a897cd9ec7589
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04111938
Reaction notes
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