Pyridine → 2-[(2-Fluorophenyl)methyl]-4,4-dimethylisoxazolidine-3,5-dione

HRID 1155465Notes

Reaction equation

N1C=CC=CC=1.[CH3:7][C:8]([CH3:15])([C:12](Cl)=[O:13])[C:9](Cl)=[O:10].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][NH:24][OH:25]>C(Cl)Cl>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][N:24]1[C:9](=[O:10])[C:8]([CH3:15])([CH3:7])[C:12](=[O:13])[O:25]1

Participants

Conditions

Temperature: -25 °C

Procedure

The procedure of Example III was utilized with 10.2 ml (0.128 mole) pyridine, 10.2 grams (0.060 mole) dimethylmalonyl chloride and 120 ml methylene chloride in solution under argon at -72° C., to which 8.5 grams (0.060 mole) of N-(2-fluorophenylmethyl)hydroxylamine (Intermediate F) in 25 ml methylene chloride was added in a single portion, raising the temperature immediately to -25° C., and stirring was continued at 0° C. for two hours. Gas chromatography on a sample of the reaction mixture showed only one major peak. The reaction mixture was washed with 2 N hydrochloric acid and water, the methylene chloride layer was separated and dried over sodium sulfate, and after removal of sodium sulfate by filtration, the solvent was removed under reduced pressure, leaving 13.0 grams of a yellow viscous liquid (91% yield). The nmr and ir spectra were consistent with the assigned structure.

Workup

additionwas added in a single portion
washThe reaction mixture was washed with 2 N hydrochloric acid and water
customthe methylene chloride layer was separated
dry with materialdried over sodium sulfate
customafter removal of sodium sulfate
filtrationby filtration
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-6137d4825332482d92380d4b5c677f2e
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04302238

Reaction notes

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