69582-93-0

Usage

Uses

Used in Pharmaceutical Development:
1-Isoquinolineacetic acid methyl ester is used as a pharmaceutical candidate for its potential therapeutic applications in treating various diseases and conditions. Its anti-inflammatory, anti-tumor, and anti-bacterial properties make it a promising agent for drug development.
Used in Organic Synthesis:
1-Isoquinolineacetic acid methyl ester is utilized as a key intermediate in organic synthesis, contributing to the creation of various chemical compounds and materials.
Used in Medicinal Chemistry:
1-Isoquinolineacetic acid methyl ester is employed as a valuable component in medicinal chemistry, where it aids in the design and synthesis of new drugs with improved therapeutic effects and reduced side effects.

InChI:InChI=1/C12H11NO2/c1-15-12(14)8-11-10-5-3-2-4-9(10)6-7-13-11/h2-7H,8H2,1H3

Upstream product

• 316790-99-5 dimethyl 2-anilino-3-(isoquinolin-1-yl)succinate 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 

Downstream Products

• 855292-39-6 isoquinolineacetic acid 
• 316790-99-5 dimethyl 2-anilino-3-(isoquinolin-1-yl)succinate 

Relevant academic research and scientific papers

The astounding chemistry of a 2-amino-1,2-dihydroisoquinoline derivative

The cycloadducts of isoquinolinium N-phenyl imide 2 with C=C bonds are derivatives of 2-amino-1,2-dihydroisoquinoline. Their Nβ-vinylphenylhydrazine system is amenable to an acid-catalyzed [3,3]-sigmatropic shift; the formation of pentacyclic aminals is exemplified by 6 → 8. The dimethyl maleate adduct 11, C21H20N2O4, is exceptional by being converted on treatment with acid to bright-yellow crystals, C24H22N2O6 (additional C3H2O2). X-Ray crystal-structure analysis and NMR spectra reveal structure 13, and mechanistic studies indicated an initial β-elimination at the N-N bond of 11 to yield 18; this step is followed by a retro-Mannich-type cleavage that gives methyl isoquinoline-1-acetate (14) and methyl 2-(phenylimino)acetate (15), according to the sequence C21H20N2O4 (11) → 18 → C12H11NO2 (14)+C9H9NO2 (15). In the second act of the drama, electrophilic attack by 15-H+ on the ene-hydrazine group of a second molecule of 11 furnishes 13 by a polystep intramolecular redox reaction. All rate constants must be fine-tuned in this reaction cascade to give 13 in yields of up to 78% with an overall stoichiometry: 2 C21H20N2O4 (11) → C24H22N2O6 (13) + C12H11NO2 (14) + aniline. Interception and model experiments confirmed the above pathway. A by-product, C33H31N3O6 (62), arises from an acid-catalyzed dimerization of 11 and subsequent elimination of 15.