Ethyl Acetate → [(4'-Fluoro-4-methylbiphenyl-3-yl)amino] (oxo)acetic acid

HRID 1963999

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=2)=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-:17].[K+].[K+].[C:22](OCC)(=[O:24])C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:22](=[O:24])[C:16]([OH:17])=[O:19])[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.0 g (9.9 mmol) of 4′-fluoro-4-methylbiphenyl-3-amine and 1.64 g (11.9 mmol) of potassium carbonate were suspended in THF, and 1.49 g (10.9 mmol) of chloroglyoxylic acid ethyl were added thereto at 0° C., and stirred at room temperature for 4 hours. After completion of the reaction, ethyl acetate was added to the mixture, and the mixture was washed with an aqueous sodium bicarbonate solution and a sodium chloride solution in this order. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 2.76 g of [(4′-fluoro-4-methylbiphenyl-3-yl)amino] (oxo)acetic acid.ethyl ester (yield: 93%).

Workup

additionwas added to the mixture
washthe mixture was washed with an aqueous sodium bicarbonate solution
dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-5096bb7463014ed393a503b841547087
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415479B2

Linked notes

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