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Acetone hydrazone

Acetone hydrazone (isopropylidenehydrazine) is the product of condensation of acetone and hydrazine, as typical for hydrazone formation. It is an intermediate in the synthesis of 2-diazopropane [fr].[2]

Acetone hydrazone can be produced on large scale by reaction of acetone azine with hydrazine, a more convenient reaction than direct reaction of acetone and hydrazine.[3] Likewise, it is susceptible to disproportionation to revert to acetone azine and hydrazine, especially in the presence of water.[3]

The chemical is one of the metabolic products of the antihypertensive pharmaceutical hydralazine, and itself also have antihypertensive effects.[4]

References

  1. ^ "Acetone hydrazone". pubchem.ncbi.nlm.nih.gov.
  2. ^ Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. (1970). "2-Diazopropane". Organic Syntheses: 27; Collected Volumes, vol. 6, 1988, p. 392.
  3. ^ a b Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Organic Syntheses; Collected Volumes, vol. 6, p. 10.
  4. ^ Cohn JN, McInnes GT, Shepherd AM (2011). "Direct-acting vasodilators". Journal of Clinical Hypertension. 13 (9): 690–692. doi:10.1111/j.1751-7176.2011.00507.x. PMC 8108999. PMID 21896152.