Acetic Acid → 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one glyoxylic acid

Reaktionsgleichung

Cl(O)(=O)(=O)=[O:2].[CH3:6][C:7]1[N:11]([CH2:12][CH:13]2[C:26](=[O:27])[C:17]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[N:24]([CH3:25])[C:16]=3[CH2:15][CH2:14]2)[CH:10]=[CH:9][N:8]=1.[C:28]([OH:31])(=[O:30])[CH3:29]>>[CH3:25][N:24]1[C:16]2[CH2:15][CH2:14][CH:13]([CH2:12][N:11]3[CH:10]=[CH:9][N:8]=[C:7]3[CH3:6])[C:26](=[O:27])[C:17]=2[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2.[C:28]([OH:31])(=[O:30])[CH:29]=[O:2]

Komponenten

Edukt 3

HCID 176Acetic Acid

HCID 4595Ondansetron

HCID 24247Perchloric Acid

Produkt 1

HCID 867486759-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one glyoxylic acid

Versuchsvorschrift

A mixture containing 2.83 g (0.01 mole) of 3-hydroxymethyl-9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one-3-glyoxylic acid lactone [compound of the formula (Ic)] and 1.64 g (0.02 mole) of 2-methylimidazole in 6.0 ml of sulfolane (tetramethylenesulfone) is heated in an oil bath of 150 to 160° C. for 15 minutes while stirring. After cooling down and diluting with 60 ml of acetone the precipitate is filtered off, washed with acetone and dried to give 0.95 g of the title compound, m.p.: 190°-200° C. (with decomposition). The active agent content of this product measured by titration with perchloric acid in glacial acetic acid was found to be 96%. In the combined filtrate of the reaction, ondansetron could be detected by thin layer chromatography. The most important characteristics of the title product are as follows: