Lithium hydroxide, monohydrate → 6-Chloro-3-(4-ethylphenylamino)benzo[d]isoxazole-7-carboxylic acid

HRID 253696Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:13]2[O:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=3)[C:9]=2[CH:8]=[CH:7][C:6]=1[Cl:23])=[O:4].O[Li].O>O1CCOCC1>[Cl:23][C:6]1[CH:7]=[CH:8][C:9]2[C:10]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:21][CH3:22])=[CH:19][CH:20]=3)=[N:11][O:12][C:13]=2[C:5]=1[C:3]([OH:4])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl-6-chloro-3-(4-ethylphenylamino)benzo[d]isoxazole-7-carboxylate (211 mg, 638 μmol) in dioxane (10.5 ml) was added a 1N aqueous solution of LiOH hydrate (134 mg, 3190 μmol) and the resulting mixture was heated to 50° C. After 1 hr, the solvent was removed in vacuo, the residue was diluted with H2O and acidified to pH2 with 2N HCl. After diluting with EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, washed with brine, dried over MgSO4, filtered and concentrated to obtain the title compound as a brown solid, which was used without further purification.

Workup

customthe solvent was removed in vacuo
additionthe residue was diluted with H2O
additionAfter diluting with EtOAc
customthe layers were separated
extractionthe aqueous layer was extracted with EtOAc (3×)
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6614d84e87124a8687ca5bb0091b0b01
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872128B2

Reaction notes

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