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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 718033Generated: October 25, 2026

Diphenyl Ether → 8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

https://huagongshe.com/reaction/718033

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiphenyl EtherHCID 7583—
ReactantN-(2-Amino-4-chlorophenyl)anthranilic acidHCID 610730—
Product8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-oneHCID 365311676.1%

Reaction Conditions

Temperature175 °C

Reaction Steps

The 2-(2-amino-4-chlorophenylamino)benzoic acid (2.00 g, 7.63 mmol) was mixed with diphenyl ether (5 mL). The reaction mixture was stirred at 175° C. for 2 hours. The mixture was cooled down to room temperature and put directly to the column eluting with 10% to 50% ethyl acetate in hexanes to afford the title compound 9 (1.42 g, 76%) as a purple solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09193749B2
Source datasetuspto-grants-2015_11
ORD IDord-b165c80520d54ac3a933ada0c4ac8d96
Source noteuspto-grants-2015_11