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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1698825Generated: November 3, 2026

Water → 4-Bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalide

https://huagongshe.com/reaction/1698825

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantThionyl ChlorideHCID 24386—
Reactant4-Methyl-2-oxo-4-phenylpentanoic acidHCID 11241195—
Reactant4-Bromo-5-aminophthalideHCID 18551168—
SolventDimethylacetamideHCID 31374—
Product4-Bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalideHCID 1855120286.5%

Reaction Steps

412 mg of 4-methyl-4-phenyl-2-oxovaleric acid is dissolved in 10 ml of dimethylacetamide and mixed under argon at −8° C. with 261 mg of thionyl chloride. After 20 minutes of stirring at −3 to +3° C., 228 mg of 4-bromo-5-aminophthalide is added. It is stirred for 1.5 hours at room temperature, then mixed with water, extracted with ethyl acetate, the organic phase is washed with water, dried (Na2SO4) and after the solvent is concentrated by evaporation and after treatment with diethyl ether, 360 mg of 4-bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalide, melting point 150-152° C., is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06344454B1
Source datasetuspto-grants-2002_02
ORD IDord-7e8237bbe35c4e429154b59af17c8d4f
Source noteuspto-grants-2002_02