Dimethylformamide → 4-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid

Reaktionsgleichung

Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=N)=[CH:6][CH:5]=1.[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14]1.C[N:21](C)C=O>N1C=CC=CC=1>[NH2:21][N:10]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([NH:3][C:13](=[O:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1

Komponenten

Versuchsvorschrift

Treatment of 4-aminobenzamidine dihydrochloride, which is commercially available, with succinic anhydride in the presence of N,N-dimethylformamide and pyridine gives 4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid, as a mixture of the zwitterion and the hydrochloride. The product is isolated from the crude reaction mixture by the addition of conc HCl in acetone followed by additional acetone. Filtration and treatment with aqueous HCl gives 4-[[4-(aminoiminomethyl)phenyl]-amino]-4-oxobutanoic, monohydrochloride.