Hydrochloric Acid → HCID 70362693, compound

Participants

Reaction Steps

3-Amino-4-[(2-bromoethyl)oxy]1,2-benzisoxazole of Example 7(a) (10.86 g, 0.0428 mole) was dissolved in 200 ml of tetrahydrofuran (THF) and 5.0 g of NaH (50% oil dispersion, 0.10 mole) was added. The reaction mixture was brought to reflux. After 30 minutes the reaction mixture was allowed to cool, an additional 1.0 g of NaH dispersion was added, and reflux was continued for 30 minutes. At the end of this time the reaction mixture was poured into H2O, acidified with concentrated hydrochloric acid, and the product extracted into ether. The organic phase was separated, dried, and concentrated, after which the residue was purified by flash chromatography (10% ethyl acetate -CH2Cl2). The material obtained in this manner retained a little yellow color, which was removed by dissolving the compound in CH2Cl2 and passing the solution over a short column of alumina. The product obtained in this manner after concentration of the solvent was recrystallized from CH2Cl2 -pentane to give 2.20 g (29%) of 4,5-dihydroisoxazolo[3,4,5-ef][1,4]benzoxazepine, mp 165°-166° C.

Provenance & Evidence