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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 249270Generated: October 26, 2026

Anthranilic Acid → 1,2,3,3a-Tetrahydro-3a-phenyl-5H-pyrrolo[1,2-a]-3,1-benzoxazin-5-one

https://huagongshe.com/reaction/249270

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAnthranilic AcidHCID 227—
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant4-ChlorobutyrophenoneHCID 253533—
SolventO-XyleneHCID 7237—
Product1,2,3,3a-Tetrahydro-3a-phenyl-5H-pyrrolo[1,2-a]-3,1-benzoxazin-5-oneHCID 19761077—

Reaction Steps

A mixture of 26.1 g of 2-aminobenzoic acid, 36.5 g of 4-chloro-1-phenyl-1-butanone, 0.5 g of p-toluenesulfonic acid and 250 ml of xylene were refluxed with a water trap. After the reaction was complete, the solvent was removed by distillation and the remaining solid was recrystallized from ethanol. Yield: 41.1 g (81.5%), melting point 152° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05214047
Source datasetuspto-grants-1993_05
ORD IDord-db75a1b05ccf4cf8acdc118e9f3e2955
Source noteuspto-grants-1993_05