7554-80-5

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-METHOXY-PHENYL)-PHTHALAMIC ACID is used as an intermediate in the synthesis of other organic compounds for its potential pharmacological properties.
Used in Drug Development:
N-(4-METHOXY-PHENYL)-PHTHALAMIC ACID is used as a histone deacetylase inhibitor and anti-inflammatory agent for its biological activities.
Used in Cancer Treatment:
N-(4-METHOXY-PHENYL)-PHTHALAMIC ACID is used in the treatment of cancer and other diseases due to its potential therapeutic effects.

Upstream product

• 85-44-9 phthalic anhydride 
• 104-94-9 4-methoxy-aniline 
• 2142-04-3 2-(4-methoxyphenyl)isoindoline-1,3-dione 

Downstream Products

• 85-44-9 phthalic anhydride 
• 104-94-9 4-methoxy-aniline 
• 2142-04-3 2-(4-methoxyphenyl)isoindoline-1,3-dione 
• 7466-55-9 3-[(4-methoxyphenyl)imino]-1(3H)-isobenzofuran-1-one 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 150772-77-3 C₁₆H₁₅NO₄ 
• 150772-78-4 C₁₇H₁₇NO₄ 
• 108444-19-5 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one 

Relevant academic research and scientific papers

Water mediated, environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamides

Water mediated and environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamide derivatives have been developed by simply combining phthalic anhydride, anilines and phenylenediammonium dihydrogenphosphate. This reaction has an easy workup, provides excellent yields, and uses water as the solvent which is considered to be relatively environmentally benign.

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.

Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.

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.

Chemoselective acylation of amines in aqueous media

Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No Chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

The cyclisation of substituted phthalanilic acids in acetic acid solution. A kinetic study of substituted N-phenylphthalimide formation

One novel and ten known substituted 3′- and 4′-phthalanilic acids have been prepared. These have been cyclised to two novel and nine known substituted N-phenylphthalimides by heating with glacial acetic acid. Both phthalanilic acids and imides have been characterised in detail and spectroscopic data are given. The kinetics of cyclisation for phthalanilic acids has been examined in detail, and it has emerged that a complex mechanism is operating. This initially involves a reversible, solvent assisted intramolecular nucleophilic attack by amide nitrogen on the carboxylic acid carbonyl. Clear evidence is seen for a long-lived intermediate as a precursor to imide formation. The observed kinetics are rationalised using a model of rapid pre-equilibration, followed by the slow breakdown of the intermediate to imide. Observed rate constants for pre-equilibration show a well behaved, linear Hammett plot (ρ = -1.1), whereas those for formation of imide do not.

Morphanthridines: Part II - Syntheses of 5,6-Dihydro-6,11-dioxomorphanthridine, 1 (or 2)-Substituted 6,11-Dioxo-5,6-dihydromorphanthridines and 7H-12,13-Dihydro-7,12-dioxobenzonaphthazepine

A novel method for the synthesis of substituted 5,6-dihydro-6,11-dioxomorphanthridines (IV) involving the cyclization of anilic acids (III) with PPA has been developed.A new heterocyclic system, 7H-12,13-dihydro-7,12-dioxobenzonaphthazepine (VII), has also been synthesized.