Oxycinchophen

Oxycinchophen is an antirheumatic agent.[1]

Oxycinchophen
Clinical data
ATC code
Identifiers
IUPAC name
  • 3-Hydroxy-2-phenyl-4-quinolinecarboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.006.932
Chemical and physical data
FormulaC16H11NO3
Molar mass265.268 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)c1c3ccccc3nc(c1O)c2ccccc2
InChI
  • InChI=1S/C16H11NO3/c18-15-13(16(19)20)11-8-4-5-9-12(11)17-14(15)10-6-2-1-3-7-10/h1-9,18H,(H,19,20) N
  • Key:XAPRFLSJBSXESP-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Synthesis
Synthesis:[2] Patent:[3]

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
  1. 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.
  2. 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.
  3. Frank J. Kreysa, et al. U.S. Patent 2,776,290 (1953 to Chemo Puro Manufacturing Corporation, Long Island, NY.).
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