Hydrochloric Acid → 3-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

HRID 1744279Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])#N.[OH-:13].[K+].[OH2:15].Cl>C(O)CO>[F:10][C:9]([F:12])([F:11])[C:8]1[C:3]([C:1]([OH:15])=[O:13])=[CH:4][N:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

3-Cyano-4-trifluoromethylpyridine (11.47 g, 66.64 mmol) was suspended in ethylene glycol (76 ml) and 85% potassium hydroxide (13.20 g, 200 mol) was added. The mixture was stirred under heating at 20° C. for 4 hours. The reaction solution was cooled to room temperature and then water (50 ml) and 4N hydrochloric acid (60 ml) were added. The resulting reaction mixture was extracted with ethyl acetate four times. The organic layers were combined, washed with saturated salt water, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 10.70 g (yield 84.0%) of the title compound.

Workup

temperatureThe reaction solution was cooled to room temperature
customThe resulting reaction mixture
extractionwas extracted with ethyl acetate four times
washwashed with saturated salt water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2ae3ab0f362642ed9142bf19a7bc83a6
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07015236B2

Reaction notes

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