369363-22-4

Upstream product

• 97-94-9 triethyl borane 
• 54723-13-6 2-(4-methoxyphenylimino)malonic acid diethyl ester 
• 104-94-9 4-methoxy-aniline 
• 609-09-6 Diethyl ketomalonate 
• 96-10-6 diethylaluminium chloride 
• 563-43-9 ethylaluminum dichloride 
• 97-93-8 triethylaluminum 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 478082-32-5 benzyl N-ethyl-N-(p-methoxyphenyl)carbamate 
• 104-48-3 4-methoxy-N-ethylaniline 

Relevant academic research and scientific papers

Conjugated imines and iminium salts as versatile acceptors of nucleophiles

Growing interests in nitrogen-containing molecules involving bioactive and functional materials have stimulated the recent development of synthetic methodologies where nucleophilic addition reactions to imino carbons are utilized in crucial steps. This article summarizes double nucleophilic addition reactions with α,β-unsaturated aldimines, addition reactions using alkynyl imines, "umpoled" reactions of α-imino esters, and the use of iminium salts as reactive electrophiles. The Royal Society of Chemistry 2009.

Iminomalonate as a convenient electrophilic amination reagent for grignard reagents

Diethyl 2-[N-(p-methoxyphenyl)imino]malonate underwent amination reactions with alkyl Grignard reagents to give N-aklylation products in good yields. The obtained N-alkylation products were readily converted into N-alkyl-panisidines by the oxidative removal of the malonate moiety. The p-methoxyphenyl group was subsequently deprotected to give primary amines.

Electrophilic amination with iminomalonate

Diethyl N-anisyliminomalonate has been found to be an excellent electrophilic amination reagent for Grignard reagents to give N-alkylated products in good yields, and subsequent air oxidation affords N-alkylanisidines.