Methylhydrazine → Trans-6-[2-(4-Hydroxyphenyl)ethenyl]-2-methyl-1(2H)-phthalazinone

Participants

Reaction Steps

Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide (15 g) was dissolved in refluxing ethanol (85 ml) and methylhydrazine (10 ml) was added slowly. The resulting suspension was refluxed for 3 hours, then cooled and filtered to give the 2-methyl-1(2H)-phthalazinone, mp 223°-225° C. The methoxy phthalazinone (10 g) was mixed with pyridine hydrochloride (35 g) and heated to 180° C. for 10 hours. The mixture was diluted with water, filtered and washed with isopropanol to give the desired phenol (4.3 g), mp 282°-284° C.

Provenance & Evidence