Oxycinchophen
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Formula | C16H11NO3 |
Molar mass | 265.268 g·mol−1 |
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Oxycinchophen is an antirheumatic agent.[1]
Synthesis
A Pfitzinger-Borsche reaction between isatin (1) and 2-methoxyacetophenone [4079-52-1] (2) catalyzed by potassium hydroxide gives 3-methoxy-2-phenylquinoline-4-carboxylic acid [41957-64-6] (3). Cleavage of the methoxy ether with hydrogen bromide completes the synthesis of oxycinchophen (4).
References
- ^ Iversen M, Munck J, Schourup K (1953). "On the toxicity of 3-hydroxy-2-phenylcinchoninic acid (oxycinchophen); histo-pathological studies in rabbits and guinea-pigs". Acta Pharmacologica et Toxicologica. 9 (3): 215–9. doi:10.1111/j.1600-0773.1953.tb02948.x. PMID 13123940.
- ^ John, Hanns (1932). "Chinolinderivate, XXXVIII. Synthese 2-phenylierter-3-Oxy-chinolin-4-carbonsäuren". Journal für Praktische Chemie. 133 (9-10): 259–272. doi:10.1002/prac.19321330902.
- ^ Frank J. Kreysa, et al. U.S. Patent 2,776,290 (1953 to Chemo Puro Manufacturing Corporation, Long Island, NY.).
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