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

HRID 1781131Notes

Reaction equation

HRID 1781131 reaction equation
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

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 756264-Aminobenzamidine dihydrochloride

Product 1

HCID 699510564-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Sources & evidence

ORD record
ord-5568f7cc89bc405daea99df6a1ff9237
Source dataset
uspto-grants-1997_05
Patent number
US05631399

Reaction notes

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