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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1475614Generated: October 31, 2026

Salicylic Acid → 2-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

https://huagongshe.com/reaction/1475614

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSalicylic AcidHCID 338—
ReactantSalicylamideHCID 5147—
ReactantThionyl ChlorideHCID 24386—
SolventO-XyleneHCID 7237—
Product2-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-oneHCID 135685723—

Reaction Conditions

Temperature37.5 °C

Reaction Steps

Xylene (1.5 L) and salicylic acid (1 Kg.) was added to a 5 L 4-neck round bottom flask equipped with a mechanical stirrer and thermocouple. Thionyl chloride (1.29 kg) was added at 10° C. to 15° C. After addition of thionyl chloride reaction mass is stirred at 10° C. to 15° C. for 30 minutes. Reaction mass is heated at 35-40° C. for 1 hr. Salicylamide solution (0.891 kg in 2.0 lit of Xylene) was added in reaction mass at 25° C.-30° C. After addition reaction mass was gradually heated at 80° C.-126° C. and stirred for 2 hrs. After the completion of reaction excess of Xylene was distilled out. Methanol was added in the reaction mass at 70° C.-80° C. and stirred for 1 hr. gradually cooled the reaction mass at 25-30° C. Filtered the solid and washed with Methanol and sucked it dry. Dry the obtained solid at 55-60° C. under vacuum tray drier.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09018389B2
Source datasetuspto-grants-2015_04
ORD IDord-b39a84a6c688470690eb53ca775c6e2c
Source noteuspto-grants-2015_04