反应详情

A mixture of 2-(3-bromobenzoyl)-3-hydroxypyridine (1.78 g), O-t-butylhydroxylamine hydrochloride (1.19 g) and ethanol (50 mL) was refluxed for 5 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate), followed by evaporating the solvent under reduced pressure. The residue was purified by means of a silica gel column (ethyl acetate--hexane) to afford (E)-2-(3-bromo-α-t-butoxyiminobenzyl)-3-hydroxypyridine (0.83 g) and (Z)-2-(3-bromo-α-t-butoxyiminobenzyl)-3-hydroxypyridine (0.83 g) and (Z)-2-(3-bromo-α-t-butoxyiminobenzyl)-3-hydroxypyridine (1.12 g) (compounds 2 and 1). In substantially the same manner as above, compounds 5, 6, 10, 13, 14, 18 to 24 were produced. Physical properties and spectrum data of these compounds and those produced in the following Examples are shown in Table 7 to Table 11.

1. temperaturewas refluxed for 5 hours
2. extractionsubjected to extraction with ethyl acetate
3. washThe extract was washed with water
4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
5. customby evaporating the solvent under reduced pressure
6. customThe residue was purified by means of a silica gel column (ethyl acetate--hexane)