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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1907776Generated: October 31, 2026

Trimethylaluminum → Methyl 11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carboxylate

https://huagongshe.com/reaction/1907776

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylaluminumHCID 16682925—
ReactantMethyl 3-amino-4-(2-(methoxycarbonyl)phenoxy)benzoateHCID 59737336—
SolventDichloromethaneHCID 6344—
ProductMethyl 11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carboxylateHCID 5973722235.3%

Reaction Steps

A solution of compound 547 (3.2 g, 10.62 mmol) and AlMe3 (6.37 mL, 12.75 mmol) in DCM (40 mL) was stirred at 45° C. for 16 h and quenched with water. The reaction was diluted with AcOEt, washed with water and 1M HCl. The organic layer was separated, dried with Na2SO4, filtered and concentrated via rotary evaporation. The residue was triturated with AcOEt, filtered, washed with AcOEt and was purified via Isco employing a 0 to 50% AcOEt in hexanes solvent gradient to afford the title compound 548 (1.01 g, 35%) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598168B2
Source datasetuspto-grants-2013_12
ORD IDord-d04079e0f1b344e3840c416539c0c3f1
Source noteuspto-grants-2013_12