Glyoxal → HCID 19101917, Verbindung

Reaktionsgleichung

N[C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].C(C=O)=O.O1C[CH2:24][CH2:23][CH2:22]1>O>[N:12]1[C:11]2[C:2](=[C:3]([C:13]([O:15][CH3:16])=[O:14])[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=2)[CH:24]=[CH:23][CH:22]=1

Komponenten

Versuchsvorschrift

A mixture of dimethyl 3,4-diaminophthalate (11.2 g, 0.05 mol) in tetrahydrofuran is treated with glyoxal (2.9 g, 0.05 mol) in water at reflux temperature, stirred for 4 hours at reflux temperature and overnight at room temperature, and concentrated in vacuo. The resultant residue is partitioned between water and methylene chloride. The organic phase is dried (MgSO4) and concentrated in vacuo to give a brown solid residue. Recrystallization from methanol gives the title product as a pink powder (9.67 g, 78.6%) mp 124°-125° C., identified by H1NMR, C13NMR, and IR spectral analyses.