1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 13958726, compound
Reaction equation
C([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:21])=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([CH3:20])[CH:14]=3)[CH:11]=2)[C:6](=[O:22])[C:5]([C:23]([OH:25])=[O:24])=[CH:4]1)C.[CH:26]1C=CC(C2C=CC=CC=2)=C[CH:27]=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[F:21][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([CH3:20])[CH:14]=1)[NH:3][CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:6]2=[O:22]Participants
Procedure
Preparation of 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylic acid was then carried out by refluxing the EMME adduct of Example 4B in Dowtherm A to produce ethyl 6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylate (Example 4C), ethylating the compound of Example 4C by heating it with ethyl iodide in dimethylformamide in the presence of anhydrous potassium carbonate to produce ethyl 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylate (Example 4D) and hydrolyzing the compound of Example 4D by refluxing it in aqueous sodium hydroxide solution containing methanol to produce 1-ethyl 6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylic acid (Example 4E).
Sources & evidence
- ORD record
- ord-a7f6bd12c82d457db06a89b83c853b02
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04699984
Reaction notes
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