Hydracarbazine

Hydracarbazine

Systematic (IUPAC) name
6-hydrazinylpyridazine-3-carboxamide
Clinical data
Identifiers
CAS Registry Number	3614-47-9
ATC code	None
PubChem	CID 71653
ChemSpider	64713
UNII	6CTK2FB9QM Y
ChEMBL	CHEMBL2106246
Chemical data
Formula	C5H7N5O
Molecular mass	153.14 g/mol

Hydracarbazine is a pyridazine that has found use as an antihypertensive agent.

Synthesis

Hydracarbazine

1. Levulinic acid is reacted with hydrazine.
2. This is aromatized to pyridazine when reacted with bromine in acetic acid. One presumes a spontaneous dehydrobromination.
3. Oxidation to the acid is accomplished with potassium dichromate, and this is esterified under Fischer conditions.
4. Conversion to chloro derivative (with POCl3) is followed by displacement with hydrazine.
5. The synthesis of blood pressure-lowering hydracarbazine is then completed by aminolysis with ammonia.

References

Liberman, D.; Rouaix, A.; Bull. Soc. Chim. Fr. 1959, 1793.