Ammonia → 3-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide

HRID 929752Notes

Reaction equation

HRID 929752 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:7]=1)=O)C.[NH3:18]>CCO>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[C:6]([C:4]([NH2:18])=[O:3])[O:10][N:9]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 136133842HCID 136133842, compound2×

Product 1

HCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amideYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 3-(4-hydroxy-phenyl)-isoxazole-5-carboxylic acid ethyl ester (which may be prepared as described in Preparation of Intermediate 1; 1.9 g, 8.15 mmol) was taken up in a solution of EtOH saturated with NH3. The mixture was stirred overnight at room temperature under nitrogen. The solvent was evaporated to give 3-(4-hydroxy-phenyl)-isoxazole-5-carboxylic acid amide (1.17 g, 70%) as a flaky white powder.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4136bbf102ee41da839f6af865efcdb8
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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