Water → 2,6-Dichloro-4-phenylnicotinonitrile
Reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=C(O)[N:3]=1.P(Cl)(Cl)([Cl:19])=O.O.[CH:23]([Cl:26])(Cl)Cl>>[Cl:19][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:23]([Cl:26])[N:3]=1Participants
Conditions
- Temperature
- 180 °C
Procedure
A mixture consisting of 42.4 gm (0.2 mol) of 2,6-dihydroxy-4-phenyl-3-cyano-pyridine and 300 ml of phosphorus oxychloride was heated for 6 hours at about 180° C. in a pressure vessel made of glass, while shaking the vessel. Thereafter, the reaction mixture was allowed to cool and was then added in small portions to a mixture of ice and water (about 3 liters), while stirring. The precipitate formed thereby was collected by suction filtration, washed with water and dried, yielding 47.4 gm (95% of theory) of the raw reaction product. The raw product was dissolved in chloroform (the small amount of insoluble matter was filtered off) and purified by passing the solution through a short silicagel column with chloroform as the flow agent. The combined chloroform fractions were evaporated, leaving as a residue 37.5 gm (75% of theory) of virtually colorless crystalline 2,6-dichloro-4-phenyl-3-cyano-pyridine of the formula ##STR5## which had a melting point of 167°-169° C.
Workup
- temperatureto cool
- stirringwhile stirring
- customThe precipitate formed
- filtrationthereby was collected by suction filtration
- washwashed with water
- customdried
- customyielding 47.4 gm (95% of theory) of the raw
- customreaction product
- filtrationwas filtered off) and
- custompurified
- customThe combined chloroform fractions were evaporated
Sources & evidence
- ORD record
- ord-9a92df4ec74b4dcfaef4845501a23f1c
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04224322
Reaction notes
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