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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 473507Generated: November 2, 2026

O-Phenylenediamine → 2-(2-Aminophenylamino)-8-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

https://huagongshe.com/reaction/473507

Reaction equation

Participants

RoleNameHCIDCharge
ReactantO-PhenylenediamineHCID 7243—
ReactantPhosphineHCID 24404—
ReactantHCID 67361741HCID 67361741—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
Solventtert-ButanolHCID 6386—
Product2-(2-Aminophenylamino)-8-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-oneHCID 6016728135%

Reaction Steps

In accordance with general method O, 0.48 g (1.8 mmol) of 2-chloro-8-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 1.05 g (9.7 mmol) of phenylenediamine, 0.04 g of Pd(OAc)2, 0.20 g of phosphine ligand and 1.65 g (17 mmol) of Na—O-tert-butylate are reacted in 10 ml of toluene and 2 ml of tert-BuOH. Purification is carried out by column chromatography (flash; SiO2; hexane 80%/ethyl acetate 20%). Yield: 35%; m.p.: 200° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633312B2
Source datasetuspto-grants-2014_01
ORD IDord-b319cb4db84943c1aac60e881e1e25c9
Source noteuspto-grants-2014_01