Lithium Hydroxide → HCID 18698582, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([I:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[C:8]([C:13]([O:15]CC)=[O:14])=[C:7]2O.C1COCC1.[Li+].[OH-]>CO.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([I:19])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:13]([OH:15])=[O:14])=[CH:7]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a solution of ethyl 8-fluoro-4-hydroxy-6-iodoquinolone-3-carboxylate (1.5 g) in 60 mL of 1:1 MeOH:THF is added 16 mL of 1M LiOH. The reaction is maintained at 40° C. overnight. The reaction mixture is cooled to room temperature, then diluted with 40 mL glacial acetic acid. The resulting precipitate is collected, washed with H2O, and dried to yield 0.890 g of 8-fluoro-6-iodoquinoline-3-carboxylic acid as a white solid. This acid (0.25 g) and 1,1'-carbonyldiimidazole (0.146 g) are dissolved in mL anhydrous THF and heated at 65° C. for 3 days. After the reaction mixture is cooled to room temperature, 4-chlorophenylhydrazine (0.161 g) and diisopropylethylamine (0.16 mL) are added. The reaction mixture is heated at 65° C. overnight to solubilize the reactants. The mixture is cooled to room temperature and partitioned between EtOAc and H2O. The aqueous layer is extracted with EtOAc (2×). The combined organic layers are washed with brine (1×), dried over Na2SO4, and condensed. The crude product is recrystallized with EtOAc/hexanes to yield 0.13g of the desired product as an off-white solid.
Workup
- temperatureThe reaction mixture is cooled to room temperature
- customThe resulting precipitate is collected
- washwashed with H2O
- customdried
Sources & evidence
- ORD record
- ord-c6296b2bd7ea4341a339d55696166780
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093732
Reaction notes
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