Process for preparation of hydrazides

Details Process for preparation of hydrazides Process for preparation of hydrazides

1996-12-12

1997-11-04

O'Sullivan, Peter

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564148, 564149, C07C24104

Patent

active

056841973

ABSTRACT:
A process for producing a hydrazide of the formula: ##STR1## is disclosed. The process comprises reacting a hydrazone of the formula: ##STR2## wherein said hydrazone is in toluene, with a mixture of Grignard reagents, wherein said Grignard reagents are in a suitable organic solvent; wherein: (A) Z is a suitable carbonyl protecting group; (B) R is a suitable --OH protecting group; (C) R.sup.1 is selected from: H, a non-enolizable alkyl, a non-enolizable substituted alkyl, aryl, substituted aryl, --S-aryl, --S-(substituted aryl), --S-alkyl, --S-(substituted alkyl), alkoxy, substituted alkoxy, aryloxy, or substituted aryloxy; (D) said mixture of Grignard reagents comprises R.sup.2 MgX in admixture with R.sup.3 MgX; (E) R.sup.2 is a suitable alkyl, substituted alkyl, alkenyl, alkynyl, aryl, substituted aryl, or aralkyl group capable of adding to the --C.dbd.N group of the hydrazone to produce the hydrazide; (F) R.sup.3 is a suitable alkyl, substituted alkyl, aryl or substituted aryl group that is more sterically hindered than said R.sup.2 group; (G) X is independently selected from Cl, Br or I for each Grignard reagent; (H) when said hydrazone is a compound of Formula 2.0 then the reaction is conducted at a temperature of about +30.degree. to about -40.degree. C.; and (I) when said hydrazone is a compound of Formula 2.1 then the reaction is conducted at a temperature of about +40.degree. to about -20.degree. C.

REFERENCES:
Alexakis et al., J. Org. Chem., "Reactivity and Diastereoselectivity of Grignard Reagents," vol. 57, No. 17 (1992).

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