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

HRID 840118Notes

Reaction equation

HRID 840118 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 870083HCID 870083, compound

Product 1

HCID 234478853-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.79 g of Compound 8C, 3.5 mL of acetic acid and 3.05 mL of 37% HCl was refluxed for 4 h. After cooling to r.t., the solvent was evaporated to dryness at reduced pressure and the crude was taken up with 15 mL of water. The precipitate was filtered off and dried to give 0.632 g (85.9%) of the title compound. M.p. 170-174° C.

Workup

  1. temperaturewas refluxed for 4 h
  2. customthe solvent was evaporated to dryness at reduced pressure
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-6510fb1badf7430e86cadcb09e049eff
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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