78987-20-9

Usage

InChI:InChI=1/C10H11NO3/c1-7-4-2-3-5-8(7)11-9(12)6-10(13)14/h2-5H,6H2,1H3,(H,11,12)(H,13,14)

Upstream product

• 104330-53-2 ethyl 3-(o-toluidino)-3-oxopropanoate 
• 141-82-2 malonic acid 
• 95-53-4 o-toluidine 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 1677-42-5 4-hydroxy-8-methyl-1,2-dihydroquinolin-2-one 
• 1846-98-6 N-(2-methylphenyl)-2-oxo-2H-chromene-3-carboxamide 
• 104330-53-2 ethyl 3-(o-toluidino)-3-oxopropanoate 
• 108621-66-5 ((Ξ)-furfurylidene)-malonic acid mono-o-toluidide 

Relevant academic research and scientific papers

Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones

Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum's acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate.

Clean and convenient one-pot synthesis of 4-hydroxycoumarin and 4-hydroxy-2-quinolinone derivatives

A simple, efficient, and environmentally friendly procedure has been developed for the reaction of Meldrum's acid with phenol, substituted phenols, aniline, or substituted anilines with Eaton's reagent (phosphoric anhydride+methylsulfonic acid) as cyclization reagent. 4-Hydroxycoumarins and 4-hydroxy-2-quinolinones were synthesized in moderate yields by carrying out the reaction in solvent-free, convenient, and clean one-pot preparation.

Lithiation of N-(2-Alkylphenyl)alkanamides and Related Compounds. A Modified Madelung Indole Synthesis

A modified Madelung synthesis for the conversion of N-(alkylphenyl)alkanamides and related compounds to indoles, benzindoles, and azindoles has been developed.This procedure consists of treating the amide with 2 or 3 equiv of n-butyllithium or lithium diisopropylamide in tetrahydrofuran at temperatures from -20 to +25 deg C.Several examples where products other than indoles were formed from the starting amide are also reported.