Studies on 3-substituted 1,2-benzisoxazole derivatives. II. The catalytic reductions of 1,2-benzisoxazole-3-acetamide oxime and related compounds.

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The hydrogenation of 1, 2-benzisoxazole-3-acetamide oxime (1) proceeded as follows. At first 1 absorbed one molar hydrogen to give 2-hydroxybenzimidoylacetamide oxime (2) and then 2 was cyclized to 3-amino-5-(2-hydroxyphenyl) isoxazole (4) which absorbed one more molar hydrogen to give 2-hydroxybenzoylacetamidine (3). The alkaline treatment of 2-hydroxybenzoylacetonitrile (11), which was obtained from 1, 2-benzisoxazole-3-acetnitrile (9) by the catalytic reduction and successive hydrolysis, gave 2-coumarinimine (12). The acidic treatment of 2-hydroxybenzimidoylacetamide (13), which was the product of the catalytic reduction of 1, 2-benzisoxazole-3-acetamide (8), afforded 4-aminocoumarin (15), an isomer of 12.

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