Hexane → 6-Hydroxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 556344Notes

Reaction equation

HRID 556344 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21]CC4C=CC=CC=4)=[CH:20][C:15]=3[O:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.CCCCCC>C1COCC1.[Pd]>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:15]=3[O:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 8058HexaneHCID 669925996-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Product 1

HCID 1363466276-Hydroxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenation of 202 mg (0.49 mMol) 6-benzyloxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide dissolved in 6 ml THF in presence of 70 mg Pd/C (10%, Engelhard 4505), filtration, concentration of the filtrate and trituration from hexane gives the title compound: MS: [M−1]=321; TLC(hexane/EtOAc 1:1): Rf=0.51.

Sources & evidence

ORD record
ord-631fbb98bc8143a09cfc3d50f09a1d21
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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