Hydrazine hydrate (1:1) → HCID 14372560, compound

Participants

Reaction Steps

A mixture of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-[3-(phthalimide)propoxy]benzamide (4.73 g, 10 mmoles) (prepared in Example 38), 64% hydrazine hydrate (800 mg, 16 mmoles) and absolute ethanol (15 ml) was heated briefly to reflux until clear solution was formed. The solution was heated 16 hours at 55°-57° C. and then 2 hours at reflux. After cooling, a solid was filtered off and washed with ethanol. The combined filtrate and washings were concentrated in vacuo. The residue was dissolved in methylene chloride, and insoluble solid removed by filtration. The filtrate was washed with water, dried and concentrated in vacuo to give a solid product. This was recrystallized from methylene chloride-n-pentane to give 2.96 g (86.3%) of the title compound as white solid, mp 119°-121° C.

Provenance & Evidence