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ChemicalBook CAS DataBase List Tert-butyl N-[(4- Methoxyphenyl)MethylaMino]carbaMate

Tert-butyl N-[(4- Methoxyphenyl)MethylaMino]carbaMate synthesis

7synthesis methods
150767-00-3 Synthesis
tert-butyl 2-(4-Methoxybenzylidene)hydrazinecarboxylate

150767-00-3
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Tert-butyl N-[(4-
Methoxyphenyl)MethylaMino]carbaMate

150767-02-5
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Yield:150767-02-5 70%

Reaction Conditions:

with palladium 10% on activated carbon;sodium formate in ethanol;water;

Steps:

3.2.4. General Procedure for the Preparation of Derivatives 1c, 8c-14c

General procedure: The hydrazones 1b, 8b-14b were subjected to catalytic reduction with Pd/C 10% (0.2 equiv.) andHCOONa (1.8 equiv.) dissolved in a 5:1 mixture of ethanol/water (1 mL/mmol). The mixture was stirredfor 1.5 h at 60 °C and then cooled down to a temperature below 40 °C and stirred for 12 h [22]. At theend of the reaction, the solution was extracted with EtOAc, dried over MgSO4, and concentratedin vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc, 8:2) in yields of 70% (1c); 70% (8c, 9c, 12c) and 65% (11c, 13c).

References:

Casanova, Bruna B.;Muniz, Mauro N.;De Oliveira, Thayse;De Oliveira, Luís Flavio;Machado, Michel M.;Fuentefria, Alexandre M.;Gosmann, Grace;Gnoatto, Simone C. B. [Molecules,2015,vol. 20,# 5,p. 9229 - 9241]