7143-42-2

Upstream product

• 67-56-1 methanol 
• 6268-38-8 N-methoxycarbonyl-anthranilic acid 
• 3481-09-2 N-chlorophthalimide 
• 2439-85-2 N-bromophthalimide 
• 118-48-9 isatoic anhydride 
• 98-94-2 N,N-dimethyl-cyclohexanamine 
• 57212-70-1 N-(mesyloxy)phthalimide 
• 79-22-1 methyl chloroformate 
• 134-20-3 2-carbomethoxyaniline 
• 56640-27-8 trans-1.4-Bis-(o-methoxycarbonylbenzoyl)-tetra-az-2-en 
• 110919-50-1 2-<((5-amino-1H-tetrazol-1-yl)carbonyl)amino>benzoic acid methyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 91-56-5 indole-2,3-dione 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 

Downstream Products

• 6268-38-8 N-methoxycarbonyl-anthranilic acid 
• 118-92-3 anthranilic acid 
• 1207-75-6 2,4-Dioxo-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinazoline 

Relevant academic research and scientific papers

Insight into the offbeat electrochemical methoxylation of isatin

A claim by Kazimierczuk and co-workers to have synthesized the diene 1 by electrochemical vic-dimethoxylation of isatin 2 is wrong. The product is now shown by a careful analysis of spectral data and synthesis to be in reality methyl N-(methoxycarbonyl)an

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins

A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.

An Electrochemical Route for Special Oxidative Ring-Opening of Indoles

A novel electrochemical protocol for the oxidative cleavage of indoles has been developed, which o?ers a simple way to access synthetically useful anthranilic acid derivatives. In undivided cells, a wide variety of indoles and alcohol compounds are examined to a?ord amide ester aromatics without using extra oxidants and stoichiometric metal catalysts, which avoids the formation of undesired by-products and exhibits high atom economy. The products we described in this perspective represent a synthetic intermediate in numerous drug molecules and industrial chemical reagents and remarkably show potential application in the future.

Oxidative Cleavage of C2-C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates

On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.

Beyond conventional routes, an unprecedented metal-free chemoselective synthesis of anthranilate esters via a multicomponent reaction (MCR) strategy

A hitherto unreported route for the synthesis of anthranilate esters is demonstrated using 2-nitrobenzaldehyde, malonitrile and an alcohol or amine via a metal and oxidant free multicomponent reaction (MCR) strategy. This process simultaneously installs an ester and urea or urethane functionality via CO and CN bond formations via concurrent oxidation of the aldehyde group and reduction of the nitro group involving an intramolecular redox process.

Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes

The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.

Effect of catalytic alkali metal bromide on Hofmann-type rearrangement of imides

The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.

4-Hydroxy-2-quinolones 173. 1-R-3-(2-diethylamino- ethyl)-1H-quinazoline- 2,4-dione hydrochlorides as potential local anesthetic agents

Different variants of the preparation and procedures in the synthesis of a series of 1-R-3-(2-dialkyl-aminoethyl)-1H-quinazoline-2,4-dione hydrochlorides having a structural similarity to the 4-hydroxy-2-quinolinone anesthetic chinoxicaine are discussed. A comparative analysis of the biological properties of the synthesized compounds and the known local anesthetics chinoxicaine and lidocaine is reported.

Selective N,N-dimethylation of primary aromatic amines with methyl alkyl carbonates in the presence of phosphonium salts

In the presence of onium salts, at 140-170 °C. methyl alkyl carbonates [1a-c, ROCO2Me, R = MeO(CH2)2[O(CH 2)2]n; n = 2-0, respectively] react with primary aromatic amines (XC6H4NH2, X = p-OMe, p-Me, H, p-Cl, p-CO2Me, o-Et, and 2,3-Me2C 6H3NH2) to yield the corresponding N,N-dimethyl derivatives (ArNMe2) with high selectivity (up to 96%) and good isolated yields (78-95%). Phosphonium salts (e.g., Ph3PEtI and n-Bu4PBr) are particularly efficient catalysts. Overall, a solvent-free reaction is coupled with safe methylating agents (1a-c) made from nontoxic dimethyl carbonate.

Selective mono-N-methylation of primary aromatic amines by dimethyl carbonate over faujasite X- and Y-type zeolites

The reaction of dimethyl carbonate (DMC) with different primary aromatic amines has been investigated under batch conditions (autoclave) in the presence of Y- and X-type zeolites. Operating at 120-150°C, highly selective mono-N-methylations are observed for anilines even when they are deactivated by either electronic effects or steric hindrance (G-C6H4NH2, G = p-NO2,p-CN, o-CO2CH3 and 2,6-dimethylaniline); typical selectivities for the formation of the corresponding mono-N-methyl derivatives [ArNH(CH3)] are in the range 92-98%, at a substrate conversion of 72-93%. A synergic effect between the reactivity of DMC (acting both as a methylating and as a reversible methoxycarbonylating agent) and the dual acid-base properties of zeolites is considered to be responsible for the unusually high selectivity observed; accordingly, a reaction mechanism is discussed, involving carbamates (ArNHCO2CH3) and N-methyl-carbamates [ArN(CH3)CO2CH3] as intermediates. The reaction is an example of a synthesis with low environmental impact: it couples the use of a non-toxic methylating agent (DMC, in place of the highly toxic methyl halides or dimethyl sulfate) with eco-friendly catalysts (zeolites) in a waste-free process.