86396-53-4

Upstream product

• 67-56-1 methanol 
• 56106-05-9 N-(4-methoxyphenyl)succinamic acid 
• 104-94-9 4-methoxy-aniline 
• 1490-25-1 succinic acid monomethylester chloride 
• 3052-50-4 monomethyl maleate 
• 3878-55-5 methyl hydrogen succinate 
• 24870-10-8 N-(4-methoxyphenyl)maleamic acid 
• 80167-51-7 (Z)-3-(4-Methoxy-phenylcarbamoyl)-acrylic acid methyl ester 

Downstream Products

• 104-94-9 4-methoxy-aniline 
• 2314-80-9 2-(4-methoxyphenyl)succinimide 
• 105461-04-9 4-Hydroxy-N-(4-methoxy-phenyl)-butyramide 
• 54660-04-7 N-(4-methoxyphenyl)pyrrolidine 

Relevant academic research and scientific papers

An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters

Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.

A facile and green synthesis of N-substituted imides

Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.

Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis of N-Substituted Cyclic Amines

Borane-methyl sulfide (BMS) reduction of variously N-substituted succinamic and glutaramic esters affords the corresponding N-substituted pyrrolidines and piperidines in high yields.The limitations, mainly caused by steric hinderance around the amine nitrogen, and putative intermediates involved in this conversion, as detected by incomplete reaction and/or synthesis followed by BMS reduction, indicate that cyclization and amide reduction successfully compete with ester reduction to afford the N-substituted cyclized amines.

FACILE ESTERIFICATION OF CARBOXYLIC ACIDS WITH ORGANOPHOSPHORUS REAGENTS. NOVEL APPLICATION OF ALKYLPHOSPHORIC ESTERS (APE)

A mixture of alkyl phosphate esters (APE) obtained from P4O10 and alkanols taken in 1:6 mole ratio is an excellent esterification reagent for several classes of carboxylic acids.This new reagent offers several advantages compared to conventional reagents.