Synthesis of benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl-

Preparation of benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl-

Preparation of benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl-

Preparation of benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl-

To a solution of 5.6 g aminoanthraquinone and 25 ml of conc. sulfuric acid at room temperature added a solution obtained by rapidly mixed 2 g of finely powdered sodium nitrite and 10 ml conc. sulfuric acid. The resulting mixture is poured into 130 g of crushed ice, the precipitated diazonium sulfate is filtered, washed with a little cold water and dissolved in a mixture of 400 ml of water and 5 ml hydrochloric acid (d 1.12). The filtered diazonium salt solution is added to a solution of 5 ml of dimethylaniline in 100 ml 5% hydrochloric acid. The mixture is cooled in ice bath and during one hour while stirring 15 ml of a saturated sodium acetate solution is added dropwise. After a few hours the formed precipitate is filtered off, washed with cold hydrochloric acid, and dried. Benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl- is purified by dissolving in a hot mixture of 300 mL alcohol and 300 ml of hydrochloric acid (d 1.19); The solution is filtered hot and poured into 1500 ml of hot 5% hydrochloric acid. After cooling, filtered, washed with 1% hydrochloric acid  and dried at room temperature. Benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl- is obtained as hydrochloride.

Л.М. Кульберг, Синтезы органических реактивов для неорганического анализа, 18-19, (1947) (LM Koulberg, Synthesis of organic reagents for inorganic analysis, 18-19, (1947))

IUPAC Name

2-[[4-(dimethylamino)phenyl]diazenyl]anthracene-9,10-dione

InChI

InChI=1S/C22H17N3O2/c1-25(2)16-10-7-14(8-11-16)23-24-15-9-12-19-20(13-15)22(27)18-6-4-3-5-17(18)21(19)26/h3-13H,1-2H3

InChI Key

HZFZIJDCKZOTBF-UHFFFAOYSA-N

Canonical SMILES

CN(C)C1=CC=C(C=C1)N=NC2=CC3=C(C=C2)C(=O)C4=CC=CC=C4C3=O

Depositor-Supplied Synonyms

NSC170660, 63040-62-0, Benzenamine, 4-((9,10-dihydro-9,10-dioxo-2-anthracenyl)azo)-N,N-dimethyl-, Benzenamine, 4-[(9,10-dihydro-9,10-dioxo-2-anthracenyl)azo]-N,N-dimethyl-, AC1L6T7N, ZINC18081429, ZINC104149159, NSC 170660, NSC-170660, 2-[(4-dimethylaminophenyl)diazenyl]anthracene-9,10-dione, 2-[(E)-(4-dimethylaminophenyl)azo]anthracene-9,10-dione, Benzenamine,10-dihydro-9,10-dioxo-2-anthracenyl)azo]-N,N-dimethyl-

Removed Synonyms

CID298495

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *