N-(3,4-Dichlorophenyl)methyl Oxamic Acid

Molecules 1997, 2, M4

N-(3,4-Dichlorophenyl)methyl Oxamic Acid

Shu-Kun Lin*

Ciba-Geigy Limited, Pharmaceuticals Division, CH-4002 Basel, Switzerland

*Present Address: Molecular Diversity Preservation International (MDPI), Saengergasse 25, CH-4054 Basel, Switzerland. Tel. +41 79 322 3379, Fax +41 61 302 8918 ([email protected])

Received: 15 January 1997 / Published: 15 April 1997

A mixture of N-(3,4-dichlorophenyl)methyl oxamic acid ethyl ester [1] (7.609 g, 27.56 mmol), ethanol (400 ml), NaOH (1N, 32 ml) and water (200ml) was stirred at r.t. overnight under N₂. HCl (2N) was added to give pH 3 followed by extraction with CH₂Cl₂(6x100 ml). The organic phases were combined, washed with water (100ml), dried (Na₂SO₄) and evaporated in vacuo to afford 6.163 g (90%) of N-(3,4-dichlorophenyl)methyl oxamic acid, a white solid.

M.p. 163deg.C (dec.).

IR (KBr): 3224, 2250, 1725 (COOH); 1690 (C=O), 1528, 1472, 1400, 1348.

¹H-NMR ((D₆)DMSO): 9.40 (bt, 1H, NH); 7.60 (d, 1H, HC(6)); 7.51 (d, 1H, HC(2)); 7.26 (q, 1H, HC(5)); 4.30 (d, 2H, CH₂).

(+)-FAB-MS: 247 (M⁺).

Acknowledgments: The author would like to thank Dr. Vittorio Rasetti for his support.

References

1. Lin, S. -K. N-(3,4-Dichlorophenyl)methyl oxamic acid ethyl ester. Molecules 1997, 2, M2.

Sample Availability: Not available.