Lithium Hydroxide → 6-Chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylic acid

HRID 1695538Notes

Reaction equation

HRID 1695538 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)=[N:7][O:8][C:4]=2[C:3]=1[C:22]([O:24]C)=[O:23].[Li+].[OH-]>O1CCOCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[CH:11]=3)=[N:7][O:8][C:4]=2[C:3]=1[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67276645Methyl 6-chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylate

Product 1

HCID 441404356-Chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 6-chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylate (1.0 g, 2.8 mmol) in dioxane (30 mL) was added a 1N solution of LiOH, monohydrate (0.59 g, 14 mmol). The reaction mixture was heated at 50° C. for 2 h. The solvent was removed and to the aqueous solution was added 2N HCl until pH 4. The precipitate formed was collected by filtration, washed with water (5 mL) and dried to give 6-chloro-3-(3-(trifluoromethyl)phenylamino)benzo[d]isoxazole-7-carboxylic acid as off-white solid.

Workup

  1. customThe solvent was removed and to the aqueous solution
  2. additionwas added 2N HCl until pH 4
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water (5 mL)
  6. customdried

Sources & evidence

ORD record
ord-f79400d1096345099284a00214fc8a4b
Source dataset
uspto-grants-2012_04
Patent number
US08163742B2

Reaction notes

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