Acetic Acid → HCID 67165343, compound

HRID 552489Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]#N)[CH:9]=2)=[CH:4][CH:3]=1.O.[C:18](O)(=[O:20])[CH3:19].C([OH:24])C>[OH-].[K+]>[CH2:18]([O:20][C:15]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:13]=[C:12]([CH3:14])[N:11]=1)=[O:24])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 0.55 g (2.6 mmol) 4-(4-Fluoro-phenyl)-6-methyl-pyridine-2-carbonitrile in 11 ml of 25% potassium hydroxide solution was heated to 100° C. for 14 h. Water (5 ml) was added and the pH adjusted to 6 by addition of acetic acid, then 10 ml of ethanol was added and the mixture was evaporated to dryness. The crude material was suspended in 30 ml of ethanol. Concentrated sulfuric acid (2 ml) were added and the suspension was refluxed for 35 h. The solution was concentrated, taken up in 20 ml of water, neutralized (pH=7-8) by addition of 5% sodium bicarbonate solution, and extracted twice with 50 ml of ethyl acetate. The combined organic phases were washed with 20 ml of water, 20 ml of brine, dried over magnesium sulfate, and concentrated in vaccuo to yield 0.42 g (1.63 mmol, 63%) of a light yellow oil which is sufficiently pure for further use in the next step, MS (ISP): m/e=260.1 (M+H)+.

Workup

customthe mixture was evaporated to dryness
additionConcentrated sulfuric acid (2 ml) were added
temperaturethe suspension was refluxed for 35 h
concentrationThe solution was concentrated
additionby addition of 5% sodium bicarbonate solution
extractionextracted twice with 50 ml of ethyl acetate
washThe combined organic phases were washed with 20 ml of water, 20 ml of brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vaccuo

Sources & evidence

ORD record: ord-86d12edede224b19affc4f18bcb51849
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951824B2

Reaction notes

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