Hydrochloric Acid → 4-Carboxy-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazole

HRID 434034

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].[OH-].[Na+].Cl>CO.C1COCC1.C(OCC)(=O)C.O>[C:3]([C:5]1[C:6]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[N:7][O:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:4])=[O:2]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-methoxycarbonyl-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazole (0.70 g, 2.1 mmol) in methanol (5 ml) and THF (2 ml) was added a solution of 2N NaOH (4 ml) at room temperature. The mixture was heated to 55° C. for 1.5 h. Upon cooling to room temperature, aqueous HCl was added until the pH was below 4. The mixture was diluted with ethyl acetate and water and the fractions separated. The organic fraction was washed (brine) and dried (MgSO4). Filtration and concentration gave the title compound (0.67 g, 100%), which was used without further purification.

Workup

temperatureUpon cooling to room temperature
customthe fractions separated
washThe organic fraction was washed (brine)
dry with materialdried (MgSO4)
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-467415632a8443a5bb32c4a832e98e6a
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670373B1

Linked notes

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