6315-89-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Aminoveratrole is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its chemical structure allows it to be a key component in the development of new pharmaceutical compounds, contributing to the advancement of medical treatments.
Used in Fine Chemicals Industry:
In the fine chemicals industry, 4-Aminoveratrole is utilized as a crucial intermediate in the production of specialty chemicals. These chemicals are often used in the formulation of various products, such as dyes, pigments, and other industrial chemicals, due to their specific properties and reactivity.
Used in Chemical Research:
4-Aminoveratrole is also employed in chemical research as a starting material for the synthesis of novel compounds and the exploration of new chemical reactions. Its unique properties make it an interesting candidate for studying various aspects of organic chemistry and potentially discovering new applications in different fields.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 4687, 1986 DOI: 10.1016/S0040-4039(00)85038-8

InChI:InChI=1/C8H11NO2/c1-10-7-4-3-6(9)5-8(7)11-2/h3-5H,9H2,1-2H3

Upstream product

• 709-09-1 3,4-dimethoxynitrobenzene 
• 2859-78-1 4-Bromoveratrole 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 1521-41-1 veratramide 
• 106107-51-1 ethyl (3,4-dimethoxyphenyl)carbamate 
• 91-16-7 1,2-dimethoxybenzene 
• 109682-63-5 (3,4-Dimethoxy-phenyl)-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester 
• 148678-88-0 C₁₄H₁₄Cl₆N₂O₆ 
• 87587-62-0 4-azido-1,2-dimethoxybenzene 
• 7664-93-9 sulfuric acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 791829-94-2 (4-methoxy-phenyl)-acetic acid-(3,4-dimethoxy-anilide) 

Downstream Products

• 856830-29-0 N-[2-(3,4-dimethoxy-anilino)-ethyl]-phthalimide 
• 57012-75-6 3-(3,4-dimethoxy-anilino)-crotonic acid ethyl ester 
• 112854-82-7 acetoacetic acid-(3,4-dimethoxy-anilide) 
• 92566-33-1 6,7-dimethoxy-2-phenylquinoline-4-carboxylic acid 
• 13548-24-8 N-(3,4-dimethoxyphenyl)-benzylidenimine 
• 39078-05-2 N-(3,4-dimethoxyphenyl)benzamide 
• 64434-49-7 3,4-dimethoxyphenylglycine 
• 62593-78-6 2-chloro-N¹-(3,4-dimethoxyphenyl)-acetamide 
• 62035-67-0 N-(3,4-dimethoxyphenyl)benzenesulfonamide 
• 100956-66-9 N-(3,4-dimethoxyphenyl)-4-methylbenzenesulfonamide 
• 18885-63-7 (3,4-dimethoxy-phenyl)-(2,4-dinitro-phenyl)-amine 
• 67278-27-7 6,7-Dimethoxy-chinolin 
• 169120-65-4 N-(3,4-dimethoxyphenyl)-2-phenylacetamide 

Relevant academic research and scientific papers

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

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.

One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.

Discovery and characterization of an acridine radical photoreductant

Photoinduced electron transfer (PET) is a phenomenon whereby the absorption of light by a chemical species provides an energetic driving force for an electron-transfer reaction1–4. This mechanism is relevant in many areas of chemistry, including the study of natural and artificial photosynthesis, photovoltaics and photosensitive materials. In recent years, research in the area of photoredox catalysis has enabled the use of PET for the catalytic generation of both neutral and charged organic free-radical species. These technologies have enabled previously inaccessible chemical transformations and have been widely used in both academic and industrial settings. Such reactions are often catalysed by visible-light-absorbing organic molecules or transition-metal complexes of ruthenium, iridium, chromium or copper5,6. Although various closed-shell organic molecules have been shown to behave as competent electron-transfer catalysts in photoredox reactions, there are only limited reports of PET reactions involving neutral organic radicals as excited-state donors or acceptors. This is unsurprising because the lifetimes of doublet excited states of neutral organic radicals are typically several orders of magnitude shorter than the singlet lifetimes of known transition-metal photoredox catalysts7–11. Here we document the discovery, characterization and reactivity of a neutral acridine radical with a maximum excited-state oxidation potential of ?3.36 volts versus a saturated calomel electrode, which is similarly reducing to elemental lithium, making this radical one of the most potent chemical reductants reported12. Spectroscopic, computational and chemical studies indicate that the formation of a twisted intramolecular charge-transfer species enables the population of higher-energy doublet excited states, leading to the observed potent photoreducing behaviour. We demonstrate that this catalytically generated PET catalyst facilitates several chemical reactions that typically require alkali metal reductants and can be used in other organic transformations that require dissolving metal reductants.

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

From alkylarenes to anilines via site-directed carbon–carbon amination

Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.

Transformation of lignin model compounds to: N -substituted aromatics via Beckmann rearrangement

Here we present the highly effective cleavage of C-C bonds in lignin model compounds for the production of N-substituted aromatics in up to 96% total yield, including benzonitriles and amides, via oxime formation followed by Beckmann rearrangement (BR). The amides could be further hydrolyzed to anilines (>92% yield) and carboxylic acids (>90% yield), respectively. In addition, the employment of a substrate with a γ-OH group will lead to the formation of C-2 monosubstituted oxazole. A one-pot process involving the BR reaction and hydrolysis has also been developed to directly afford an up to 96% total yield of benzonitriles, benzamides, and anilines. This strategy enabled us to successfully apply the BR reaction to the degradation of lignin model compounds to N-functionalized aromatic products under mild conditions.

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.