136-90-3

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-2-METHYLANISOLE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, specifically in the preparation of triamine pyrimidine derivatives. These derivatives have demonstrated potential as antitumor agents, making 4-AMINO-2-METHYLANISOLE a valuable component in the development of novel cancer treatments.
In the context of cancer research and drug development, 4-AMINO-2-METHYLANISOLE serves as a key building block for creating new molecules with potential antitumor activities. Its unique structure allows for the formation of various triamine pyrimidine derivatives, which can be further modified and optimized to enhance their therapeutic effects against different types of cancer.
The use of 4-AMINO-2-METHYLANISOLE in the pharmaceutical industry highlights its importance as a versatile and promising compound for the development of innovative cancer therapies. As research continues to explore its potential applications, it is likely that 4-AMINO-2-METHYLANISOLE will play a significant role in the advancement of cancer treatment options.

Synthesis

The synthesis of 4-methoxy-3-methylaniline is as follows:4-Methoxy-3-methyl-phenylamine10% Palladium on carbon (10% Pd/C) (1.5 g) was added to a solution of 1 -methoxy-2- methyl-4-nitrobenzene (9.5 g, 57 mmol) in methanol (100 ml_). The mixture was stirred under a hydrogen atmosphere (1 atm.) at room temperature for 16 h. The mixture was filtered through a pad of CELITE and the filtrate was evaporated in vacuo to yield 4- methoxy-3-methylphenylamine (8.0 g, 57 mmol, 100%).

InChI:InChI=1/C8H11NO/c1-6-5-7(9)3-4-8(6)10-2/h3-5H,9H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 4113-72-8 1-azido-3-methylbenzene 
• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 50741-92-9 2-methyl-4-nitroanisole 
• 31910-25-5 N-(4-methoxy-3-methylphenyl)acetamide 
• 578-58-5 2-methylmethoxybenzene 
• 16375-90-9 4-acetamido-2-methylphenol 
• 2835-96-3 4-amino-2-methylphenol 
• 99-53-6 2-methyl-4-nitrophenol 
• 7439-89-6 iron 
• 108-39-4 3-methyl-phenol 
• 14786-82-4 4-hydroxy-2-methylanisole 

Downstream Products

• 31910-25-5 N-(4-methoxy-3-methylphenyl)acetamide 
• 14786-82-4 4-hydroxy-2-methylanisole 
• 64180-05-8 2-[(4-Methoxy-3-methyl-phenylamino)-methylene]-malonic acid diethyl ester 
• 32323-40-3 4-methoxy-3,N,N-trimethyl-aniline 
• 916513-24-1 (2-amino-5-methoxy-4-methyl-phenyl)cyclohexylmethanone 
• 645419-16-5 2-bromo-4-methoxy-5-methylacetanilide 
• 1228365-48-7 C₁₂H₁₄ClNO₃ 
• 1354188-15-0 (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)ethyl pivalate 
• 1354188-17-2 (S)-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one 
• 1354189-00-6 (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate 
• 1354189-03-9 (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-vinylquinolin-6-yl)ethyl pivalate 

Relevant academic research and scientific papers

Transition metal-diene complexes in organic synthesis, Part 22. The iron-mediated quinone imine cyclization: A general route to 3-hydroxycarbazoles

Electrophilic aromatic substitution of 4-methoxyarylamines 2 by the tricarbonyliron-complexed cyclohexadienylium cations 1 leading to the iron complexes 3 is described. Chemoselective oxidation of the arylamine moiety of the complexes 3 to the quinone imine and iron-mediated quinone imine cyclization using appropriate oxidizing reagents (activated manganese dioxide or thallium(III) trifluoroacetate) led to the tricarbonyliron-complexed 4b,8a-dihydrocarbazol-3-ones 5. Demetalation of 5 with trimethylamine N-oxide at room temperature occurred with concomitant aromatization of the organic ligand and provided a broad access to the 3-hydroxy-9H-carbazoles 7.

C-H Amination of Arenes with Hydroxylamine

This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.

Palladium supported on metal–organic framework as a catalyst for the hydrogenation of nitroarenes under mild conditions

Sustainable development demands an environmentally friendly and efficient method for the hydrogenation of organic molecules, including the hydrogenation of functionalized nitroarenes. In this study, a highly active and selective metal–organic framework-supported palladium catalyst was prepared for the catalytic hydrogenation of nitroarenes. High selectivity (>99%) and excellent yield (98%) of aniline were realized after 2 hours in ethanol under hydrogen (1 atm) at room temperature. The reductions were successfully carried out in the presence of a wide range of other reducible functional groups. More importantly, the catalyst was very stable without the loss of its catalytic activity after five cycles.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.

Enantioselective Synthesis of (+)-Mitomycin K by a Palladium-Catalyzed Oxidative Tandem Cyclization

The mitomycins, a family of bioactive natural products, feature a compact 6/5/5-fused polycyclic ring structure densely decorated with highly reactive and/or fragile quinone, amino ketal, and aziridine as well as carbamate moieties. It is this striking feature that has defeated numerous synthetic attempts towards these apparently small molecules, rendering them one of the most formidable targets for total synthesis. We herein report the first enantioselective synthesis of (+)-mitomycin K, a representative of G series mitomycins. The key step of this synthesis is an enantioselective oxidative cyclization catalyzed by a palladium/(+)-sparteine system that had previously been developed by our group. The robustness of this method bodes well for further applications in the asymmetric total synthesis of natural products, particularly those with characteristic 6/5/5-fused pyrroloindole skeletons.

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

Direct metal-free synthesis of diarylamines from 2-nitropropane via the twofold C-H functionalization of arenes

Synthesis of symmetric diarylamines via a twofold intermolecular electrophilic C-H functionalization of electron-rich arenes by umpolung-activated nitroalkane in polyphosphoric acid is demonstrated.

Electrochemical C-H amination: Synthesis of aromatic primary amines via N -arylpyridinium ions

We have developed a new method for C-H amination of aromatic compounds based on electrochemical oxidation of aromatic compounds in the presence of pyridine followed by the reaction of the resulting N-arylpyridinium ions with an alkylamine. This new transformation serves as a powerful method for synthesizing aromatic primary amines from aromatic compounds without using metal catalysts and harsh chemical reagents. High chemoselectivity of the present method is demonstrated by C-H amination of aromatic compounds bearing a nitro group to give a key intermediate for the synthesis of VLA-4 antagonist.

2- (TERT - BUTOXY) -2- (7 -METHYLQUINOLIN- 6 - YL) ACETIC ACID DERIVATIVES FOR TREATING AIDS

The invention provides compounds and salts thereof as d herein. The invention also provides pharmaceutical compositions comprising a compound disclosed herein, processes for preparing compounds disclosed herein, intermediates useful for preparing compound

2 -QUINOLINYL- ACETIC ACID DERIVATIVES AS HIV ANTIVIRAL COMPOUNDS

The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful fo