3556-86-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-HYDROXY-4-METHYLBENZOATE is used as an intermediate in the synthesis of potent antimalarial agents. Its unique chemical structure contributes to the development of effective drugs against malaria, a disease that affects millions of people worldwide.
Used in Chemical Industry:
METHYL 3-HYDROXY-4-METHYLBENZOATE is used as a precursor in the preparation of aromatic inhibitors of anthranilate synthase. Anthranilate synthase is a key enzyme involved in the biosynthesis of tryptophan, an essential amino acid. Inhibiting this enzyme can have potential applications in various fields, such as agriculture and medicine, by targeting specific metabolic pathways in pests or pathogens.

Synthesis

Methyl 3-hydroxy-4-methylbenzoate is synthesized by the following steps:The amino ester 35 (60 g, 0.364 mol) was added to dil. H2SO4 (125 ml ?conc. H2SO4 diluted with 1 L water) and warmed on a water bath until all ?the compound was dissolved. Cold water (800 ml) was added and the ?mixture was cooled to 0 °C. NaNO2 (62.6 g, 0.907 mol) was added to this ?mixture with constant stirring. It was then stirred at room temperature for 15 minutes. ?Then, urea (65.4 g, 1.09 mol) was added in portions. The mixture was warmed at 50 oC for ?15 minutes (temperature was not allowed to rise above 55 oC). EtOAc was added to the?reaction mixture and washed with brine, dried (anhydrous Na2SO4), filtered and ?concentrated under reduced pressure to afford a colourless solid (26.56 g).

InChI:InChI=1/C8H8O3/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4,9H,1H3,(H,10,11)/p-1

Upstream product

• 118446-42-7 3-methoxycarbonylhepta-3,5-dienoic acid 
• 67-56-1 methanol 
• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 186581-53-3 diazomethane 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 
• 18595-18-1 3-amino-4-methyl benzoic acid methyl ester 
• 99-75-2 4-methyl-benzoic acid methyl ester 

Downstream Products

• 869892-67-1 3-(1-methoxycarbonyl-ethoxy)-4-methylbenzoic acid methyl ester 
• 159640-54-7 methyl 4-methyl-3-trifluoromethanesulfonyloxybenzoate 
• 895240-72-9 3-(3-methoxy-propoxy)-4-methyl-benzoic acid methyl ester 
• 865138-66-5 methyl 3-isopropoxy-4-methylbenzoate 
• 104224-53-5 methyl 3-(p-t-butylbenzoyloxy)-4-methyl benzoate 
• 87808-14-8 4-methyl-3-hydroxyethylbenzoate 
• 87808-27-3 Methyl 2-bromo-5-hydroxy-4-methylbenzoate 
• 39635-23-9 3-hydroxy-4-methyl-benzoic acid hydrazide 
• 886858-77-1 methyl 3-(difluoromethoxy)-4-methylbenzoate 
• 1215031-47-2 Methyl 4-methyl-3-[2-(4-methyl-piperazin-1-ylmethyl)-pyrimidin-4-yloxy]-benzoate 
• 1017082-78-8 methyl 3-benzyloxy-4-methyl-benzoate 
• 137960-09-9 4-Methyl-3-phenoxy-benzoic acid methyl ester 
• 204568-74-1 methyl 3-acetyloxy-4-methylbenzoate 
• 183153-23-3 methyl 3-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)methyloxy]-4-methylbenzoate 

Relevant academic research and scientific papers

Rhodium-Catalyzed Twofold Unsymmetrical C-H Alkenylation-Annulation/Thiolation Reaction to Access Thiobenzofurans

A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed, enabling the straightforward and efficient synthesis of various thiobenzofurans in one step. This robust protocol proceeds with a broad substrate scope and good functional group tolerance under relatively mild reaction conditions.

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Sulfoximine-Assisted One-Pot Unsymmetrical Multiple Annulation of Arenes: A Combined Experimental and Computational Study

Discussed herein is an unprecedented Ru-catalyzed one-pot unsymmetrical C-H difunctionalization of arenes comprising intramolecular hydroarylation of olefins and intermolecular annulation of alkynes. This unprecedented 2-fold C-H functionalization is validated on the basis of experimental and density functional theory (DFT) study. The transformation readily occurs with the assistance of methylphenyl sulfoximine (MPS) directing group in the presence of Ru catalyst forming two C-C and one C-N bonds in a single operation. The overall process is atom economical and step-efficient and provides unusual dihydrofuran-fused isoquinolone heterocycles. Further annulation of NH and the proximal o-C-H-arene of isoquinolone with alkynes build highly conjugated novel polycyclic compounds. Overall, three independent annulations in arene motifs are visualized and thoughtfully executed; finally, 5 ring-fused structural entities are constructed forming three C-C and two C-N bonds.

NOVEL INHIBITORS OF MAP4K1

The invention relates to novel inhibitors of MAP4K1 (HPK1) useful for the treatment of diseases or disorders characterised by dysregulation of the signal transduction pathways associated with MAPK activation, including hyperproliferative diseases, diseases of immune system dysfunction, inflammatory disorders, neurological diseases, and cardiovascular diseases. The invention further relates to pharmaceutical compositions comprising the same and methods of treatment of said diseases and disorders. The inhibitors are of formula (I) wherein the definitions for A, D, E, F, R5, R6, R7, Z, ring Q, n, x and y are as given in the application.

A convenient synthesis of phenols

Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.

Ruthenium-Catalyzed Hydroarylation and One-Pot Twofold Unsymmetrical C?H Functionalization of Arenes

A methyl phenyl sulfoximine (MPS) is used as a directing group in the ruthenium-catalyzed intramolecular hydroarylation of alkene-tethered benzoic acid derivatives to afford dihydrobenzofurans and indolines in good to excellent yields. A one-pot, unsymmetrical, twofold C?H functionalization involving intramolecular C?C and intermolecular C?C/C?N bond formations is successfully demonstrated by using a single set of catalytic reaction conditions, which is unprecedented thus far. A novel isoquinolone-bearing dihydrobenzofuran is constructed through an unsymmetrical twofold C?H functionalization.

BENZAMIDE CGRP RECEPTOR ANTAGONISTS

The present invention is directed to benzamide compounds which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.

Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection

The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds.

NEW BENZIMIDAZOLE DERIVATIVES

The invention is concerned with novel benzimidazole derivatives of Formula (I) wherein A, n and R1 to R7 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds act on Farnesyl X receptor (FXR) and against cholesterol and lipid illnesses, diabetes, obesity, psoriasis, cancer, osteoporosis, Parkinson's and Alzheimer's disease.