Acylhydrazine

An example of an acylhydrazine. This compound has been called acetylhydrazide, acetohydrazide, or acetic acid hydrazide.^[1]

An acylhydrazine is analogous to an amide, but the -OH portion of a carboxylic acid is replaced by hydrazine rather than ammonia (one less hydrogen at the point of attachment). Acylhydrazines are a type of hydrazides.

Acylhydrazines are intermediates in chemical syntheses. For example, a synthesis of sunitinib begins by mixing 5-fluoroisatin slowly into hydrazine hydrate.^[2] After 4 hours at 110 °C, the indole ring structure has been broken into (2-amino-5-fluoro-phenyl)-acetic acid hydrazide with reduction of the ketone at the 3-position. Subsequent annelation in strong acid creates the 1,3-dihydro-2-oxo indole structure required for the drug.

References

1. "ChemicalBook:2-(4-ethylphenoxy)acetylhydrazide".
2. "US patent 6573293".