Water → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid

HRID 1726984Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH2:8][C:9]#N)=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:3]=1.[OH-:21].[Na+].[OH2:23]>C(O)CC>[CH3:1][C:2]1[C:7]([CH2:8][C:9]([OH:23])=[O:21])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 25 g (90 mmol) of the above prepared [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetonitrile, 20 g of sodium hydroxide (500 mmol), 60 ml of water and 250 ml of propanol was stirred vigorously at 100° C. Hydrolysis was complete after 2 hours. The reaction mixture was then evaporated to dryness and the residue was dissolved in 70 ml of water; then, 60 ml of cold 8 N aqueous HCl was added and the acid was extracted with three portions of 250 ml of ethyl acetate; the combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to dryness. 25.1 g of the title product was obtained as pale yellow solid.

Workup

additionA mixture of 25 g (90 mmol) of the
customHydrolysis
customThe reaction mixture was then evaporated to dryness
dissolutionthe residue was dissolved in 70 ml of water
additionthen, 60 ml of cold 8 N aqueous HCl was added
extractionthe acid was extracted with three portions of 250 ml of ethyl acetate
washthe combined organic phases were washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-557651c5f7264a43bbb6a262264f41bd
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495001B2

Reaction notes

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