Hydrochloric Acid → 3-(2-Fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid

HRID 434029

Reaction equation

HRID 434029 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:7][O:8][C:9]=1[CH3:10])=[O:4].CO.[OH-].[Na+].Cl>O>[C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:7][O:8][C:9]=1[CH3:10])([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18756272Methyl 3-(2-fluorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 64841013-(2-Fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acidYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-methoxycarbonyl-5-methyl-3-(2-fluorophenyl)isoxazole (2.20 g, 8.84 mmol), MeOH (25 ml), and 2N NaOH (8.8 ml) was heated at 50° C. overnight (19 h). The reaction was cooled to room temperature, diluted with H2O, and acidified (2N HCl) to less than pH 3. The mixture was extracted with EtOAc (twice) and the combined extracts were washed (brine), dried (MgSO4), filtered, and concentrated to give the title compound (1.88 g, 96%). This material was used without further purification.

Workup

  1. extractionThe mixture was extracted with EtOAc (twice) and the combined extracts
  2. washwere washed (brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e39a911cdc174001b9a03a0ff5720557
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Linked notes

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