ChemicalBook CAS DataBase List BENZO[D]ISOXAZOL-3-OL

BENZO[D]ISOXAZOL-3-OL synthesis

4synthesis methods

Product Name:BENZO[D]ISOXAZOL-3-OL
CAS Number:21725-69-9
Molecular formula:C7H5NO2
Molecular Weight:135.12

89-73-6
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21725-69-9
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Yield: 100%

Reaction Conditions:

Stage #1:salicylhydroxamic acid with 1,1'-carbonyldiimidazole in tetrahydrofuran at 60; for 2.5 h;Heating / reflux;
Stage #2: with hydrogenchloride in water; pH=2 at 10 - 15; for 0.5 h;

Steps:

A1.b
A solution of intermediate 1 (1,92 M in THF) was stirred at 60°C. A solution of CDI (3,84 M in THF) was added over 30 min. under reflux to the aforementioned solution and refluxed for another 2 hours at 60°C. The reaction mixture was cooled to 40°C and the solvent evaporated. After completion, the remaining residue was quenched with water and acidified with 12N HCI to pH 2. The mixture was stirred for 30 min. at 10- 15°C and the resulting precipitate filtrated, washed with ice-water and dried under reduced pressure at 90 °C. Quantitative Yielding 3-Hydroxybenzisoxazole (intermediate 2).

References:

JANSSEN PHARMACEUTICA N.V. WO2005/89753, 2005, A2 Location in patent:Page/Page column 27

119-36-8 Synthesis