Aniline → Anthraquinone

HRID 1110949Notes

Reaction equation

HRID 1110949 reaction equation
N[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](NC2C(C)=C(S(O)(=O)=O)C(C)=C(N)C=2C)=[CH:4][C:3]=1S(O)(=O)=O.N1C(Cl)=NC(Cl)=NC=1Cl.NC1C=CC=CC=1>>[CH:9]1[C:8]2[C:7](=[O:17])[C:6]3[C:15](=[CH:2][CH:3]=[CH:4][CH:5]=3)[C:14](=[O:16])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 7954Cyanuric chlorideHCID 903682-Anthracenesulfonic acid, 1-amino-4-[(3-amino-2,4,6-trimethyl-5-sulfophenyl)amino]-9,10-dihydro-9,10-dioxo-

Product 1

HCID 6780Anthraquinone

Procedure

1-Amino-4-(3'-amino-2',4',6'-trimethyl-5'-sulfoanilino)anthraquinone-2-sulfonic acid (23.7 parts), cyanuric chloride (9.3 parts) and 1-aminobenzene-3-β-sulfatoethylsulfone (14.1 parts) were subjected to condensation in an aqueous medium one after another in a usual manner. Successively, the resulting condensate was further subjected to condensation with aniline (4.7 parts) at 60° to 70° C. under a weak acid condition. Thereafter, the reaction mixture was salted-out to separate crystals, thereby obtaining an anthraquinone compound of the following formula in the free acid form. ##STR264##

Workup

  1. customto separate crystals

Sources & evidence

ORD record
ord-5e592fc7519b4951b3dc8d79e6dea564
Source dataset
uspto-grants-1990_12
Patent number
US04977261

Reaction notes

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