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

HRID 473507Notes

Reaction equation

HRID 473507 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].P>C1(C)C=CC=CC=1.C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:27][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 7243O-PhenylenediamineHCID 24404PhosphineHCID 67361741HCID 67361741, compound

Product 1

HCID 601672812-(2-Aminophenylamino)-8-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-oneYield 35%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

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.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-b319cb4db84943c1aac60e881e1e25c9
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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