Sulfuric acid magnesium salt (1:1) → N'-(propan-2-ylidene)(tert-butoxy)carbohydrazide

HRID 624615Notes

Reaction equation

HRID 624615 reaction equation
Cl.[CH:2]([NH:5][NH2:6])([CH3:4])[CH3:3].[C:7](NN)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].S([O-])([O-])(=O)=O.[Mg+2]>CC(C)=O>[CH3:3][C:2](=[N:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:4]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70091tert-Butyl carbazateHCID 855731-Isopropylhydrazine hydrochloride

Product 1

HCID 11435207N'-(propan-2-ylidene)(tert-butoxy)carbohydrazide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Scheme 1 shows the synthesis of intermediate isopropylhydrazine hydrochloride 4 from Boc-hydrazine 1. Condensation of 1 with acetone and magnesium sulfate gave Boc-hydrazone, tert-butyl 2-(propan-2-ylidene)hydrazinecarboxylate 2 (Example 1). Palladium-catalyzed hydrogenation of 2 in acetic acid and methanol gave Boc-isopropyl-hydrazine 3 (Example 2) which was treated in situ with hydrogen chloride gas to give 4 (Example 3).

Sources & evidence

ORD record
ord-738cde7903ee4c358b0e9090431a3e9d
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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