BENZO[D]ISOXAZOL-3-OL synthesis
- Product Name:BENZO[D]ISOXAZOL-3-OL
- CAS Number:21725-69-9
- Molecular formula:C7H5NO2
- Molecular Weight:135.12
89-73-6
21725-69-9
The general procedure for the synthesis of benzo[D]isoxazol-3-ol from salicylhydroxamic acid is as follows: intermediate 1 (1.92 M in THF solution) was placed in a reaction vial and stirred at 60 °C. CDI (3.84 M, THF solution) was added slowly over 30 minutes. The reaction mixture was heated to reflux and reflux was continued at 60 °C for 2 hours. Upon completion of the reaction, the mixture was cooled to 40 °C and subsequently evaporated to remove the solvent. The residue was quenched with water and the pH was adjusted to 2 with 12 N HCl. The mixture was stirred for 30 min followed by filtration at 10-15 °C to collect the precipitate. The precipitate was washed with ice water and finally dried under reduced pressure at 90 °C to give 3-hydroxybenzisoxazole (Intermediate 2) in quantitative yield.
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
1030 suppliers
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21725-69-9
126 suppliers
$16.96/250mgs:
89-73-6
258 suppliers
$14.00/5g
21725-69-9
126 suppliers
$16.96/250mgs:
69-72-7
1302 suppliers
$5.00/10g
21725-69-9
126 suppliers
$16.96/250mgs: