|Systematic (IUPAC) name|
|CAS Registry Number|
|Molecular mass||255.27 g/mol|
|(what is this?)|
The starting N-amino-2-indolone (1) can be obtained by reduction of the N-nitrosation product of Oxindole (2-indolone) itself. Reaction of this intermediate, which is in essence an N-acylhydrazine, with phenylacetone gives the corresponding hydrazone (2). The hydrazone is then treated with ethanolic hydrogen chloride; Fischer indole synthesis would in theory lead to the fused bicyclic indole (3). The observed product (4) can be rationalized by assuming that the labile bicyclic N-acyl indole opens to an ester in the presence of ethanolic HCl. Ozonation of the double bond in the heterocyclic ring then leads to N-acylated benzophenone 5, with the acetyl group arising from the ring atom bearing a methyl group. Acid hydrolysis of this intermediate removes both the amide and the ester to afford amfenac.
- Bromfenac (same structure as amfenac but with p-bromo)
- Welstead, W. J.; Moran, H. W.; Stauffer, H. F.; Turnbull, L. B.; Sancilio, L. F. (1979). "Antiinflammatory agents. 1. Synthesis and antiinflammatory activity of 2-amino-3-benzoylphenylacetic acid". Journal of Medicinal Chemistry 22 (9): 1074–9. doi:10.1021/jm00195a012. PMID 490552.
- W. J. Welstead, H. W. Moran, DE 2324768 C.A. 80, 59708s (1974) and U.S. Patent 4,045,576 (1973, 1977 both to A. H. Robbins)
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