1,5-Dichloroanthraquinone → HCID 21489835, compound

HRID 1973621Notes

Reaction equation

HRID 1973621 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].Cl[C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[C:18](Cl)[CH:19]=[CH:20][CH:21]=3)[C:16](=[O:27])[C:15]=2[CH:14]=[CH:13][CH:12]=1>[Cu]>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH:4][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[C:18]([NH:4][C:3]4[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:2]=4[Cl:1])[CH:19]=[CH:20][CH:21]=3)[C:16](=[O:27])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 67111,5-DichloroanthraquinoneHCID 72622,5-Dichloroaniline

Product 1

HCID 21489835HCID 21489835, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

If, analogously to the above example, 2,5-dichloroaniline is condensed with 1,5-dichloroanthraquinone in the presence of a mixture of 0.5 part of copper powder and 0.5 part of copper-I chloride as the catalyst, instead of the copper-I iodide/picoline complex, only 12 parts of 1,5-bis-(2,5-dichloroanilino)anthraquinone are obtained, corresponding to a yield of only 23%.

Sources & evidence

ORD record
ord-4c89703cfee445fc9138ee966f5973ca
Source dataset
uspto-grants-1976_12
Patent number
US03998780

Reaction notes

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