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

HRID 1242315Notes

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 compound 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 to yield 25.1 g of the title product 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 compound 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-7d3938b959e44481aecff6ef8beac118
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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