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 (less one hydrogen at the point of attachment).

For example, the alternate synthesis of sunitinib from US patent 6573293^[2] begins by mixing 5-fluoroisatin slowly into hydrazine hydrate. 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

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