O-Phenylenediamine → 8-(2-Aminophenylamino)-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

HRID 473470Notes

Reaction equation

HRID 473470 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:19]=1.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].P.O(C(C)(C)C)[Na]>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:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:19]=1

Participants

8

Reactant 4

HCID 7243O-PhenylenediamineHCID 24404PhosphineHCID 67360944HCID 67360944, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 452806418-(2-Aminophenylamino)-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 3

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

Procedure

For the synthesis of the title compound, 0.54 g (0.0020 mol) of 8-chloro-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 1.08 g (0.010 mol) of phenylenediamine, 2 spatula tips of Pd(OAc)2, 0.14 g of phosphine ligand and 1.60 g (0.0166 mol) of NaOtert-Bu in 10 ml of toluene and 2 ml of tert-BuOH are reacted by method O. Purification is carried out by column chromatography (flash; SiO2; hexane 80%/ethyl acetate 20%). C22H20N2O2 (Mr=344.42)

Sources & evidence

ORD record
ord-3204d51816b14fc18ee96eac421fc3bf
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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