Acetic Acid → tert-butyl 2-ethylhydrazinecarboxylate

HRID 1062326Notes

Reaction equation

HRID 1062326 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[CH:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.O=[Pt]=O>[C:1]([O:5][C:6]([NH:8][NH:9][CH2:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57358255tert-Butyl 2-ethylidenehydrazine-1-carboxylate

Product 1

HCID 11194489tert-butyl 2-ethylhydrazinecarboxylateYield 97.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A slurry of N′-ethylidene-hydrazinecarboxylic acid tert-butyl ester (5.0 g, 32 mmol), acetic acid (48 μL) and PtO2 (250 mg) in ethanol (50 mL) was shaken under a 40 psi pressure of H2 in a Parr hydrogenator for 24 h. The mixture was filtered through Celite to provide N′-ethylhydrazinecarboxylic acid tert-butyl ester (5 g) as a clear oil. MS (ESI+) for C7H16N2O2 m/z 161.0 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite

Sources & evidence

ORD record
ord-846c360a658f4784b9fa1581d32e86d1
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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