Lithium Hydroxide → HCID 178427815, compound

HRID 2289942Notes

Reaction equation

HRID 2289942 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[C:8]([C:13]([O:15]CC)=[O:14])=[C:7]2[OH:18].C1COCC1.[Li+].[OH-]>CO.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH3:19])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:13]([OH:15])=[O:14])=[C:7]2[OH:18]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 54737845HCID 54737845, compound

Product 1

HCID 178427815HCID 178427815, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 8-fluoro-4-hydroxy-6-methylquinolone-3-carboxylate (0.50 g) in 30 mL of 1:1 MeOH:THF is added 8 mL of 1M LiOH. The reaction is maintained at 40° C. overnight. The reaction mixture is cooled to room temperature, then diluted with 20 mL glacial acetic acid. The resulting precipitate is collected, washed with H2O, and dried to yield 0.382 g of 8-fluoro-4-hydroxy-6-methyl-3-quinolinecarboxylic acid as a white solid. To a solution of this acid (0.23 g) and 4-chlorophenylhydrazine (0.21 g) in 10 mL DMF is added triethylamine (0.16 m), EDC (0.24 g), and HOBt (0.16 g). The mixture is stirred at room temperature for 3 days. Upon diluting the reaction mixture with 100 mL H2O, an orange solid precipitates. The crude product is adsorbed onto silica and chromatographed eluting with 4% MeOH in CHCl2. Fractions homogenous by TLC are condensed and recrystallized from EtOAc/hexanes to yield 0.0181 g of the desired product as a white solid.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customThe resulting precipitate is collected
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-9829031a04064041bab609c42d8c91e9
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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