Water → 3-Chloro-2-(4-cyano-3-nitrophenyl)-5-trifluoromethylpyridine

HRID 1957271Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15](F)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C-:22]#[N:23].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([C:22]#[N:23])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

5.0 g of 3-chloro-2-(4-fluoro-3-nitrophenyl)-5-trifluoromethylpyridine and 1.5 g of potassium cyanide in 50 ml of dimethylformamide were heated at 50° C. for 4 hours and then stirred at 23° C. for 20 hours. The mixture was then poured into 200 ml of water. The aqueous phase was extracted three times with 100 ml of tertbutyl methyl ether each time. The combined organic phases were washed twice with 50 ml of water each time, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=9:1). Yield: 2.7 g (53%) of a yellow oil which slowly crystallized.

Workup

extractionThe aqueous phase was extracted three times with 100 ml of tertbutyl methyl ether each time
washThe combined organic phases were washed twice with 50 ml of water each time
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=9:1)
customYield: 2.7 g (53%) of a yellow oil which slowly crystallized

Sources & evidence

ORD record: ord-6ede41fbbc33493494ca78ea9791b82c
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783522

Reaction notes

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