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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 560271Generated: October 29, 2026

Chloroacetyl chloride → Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

https://huagongshe.com/reaction/560271

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroacetyl chlorideHCID 6577—
ReactantPotassium CarbonateHCID 11430—
ReactantMethyl 3-amino-2-hydroxybenzoateHCID 12782444—
SolventDimethylformamideHCID 6228—
ProductMethyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylateHCID 23770643—

Reaction Steps

At RT chloro-acetyl chloride (29.0 mmol) is added dropwise to a solution of 3-amino-2-hydroxy-benzoic acid methyl ester (26.4 mmol) in DMF (100 mL). After 20 min K2CO3 (126 mmol) is added portionwise, the mixture is stirred for 16 h at RT and the solvents are removed in vacuo. Water and DCM are added, the layers are separated and the organic layer is washed with brine and dried over Na2SO4. The solvents are removed in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.68 min; [M+H]+=208.0.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08063099B2
Source datasetuspto-grants-2011_11
ORD IDord-84b07eefd193462383f41501944ee39c
Source noteuspto-grants-2011_11