6375-47-9

Basic information

• Product Name: 3'-Amino-4'-methoxyacetanilide
• Synonyms: 2-AMINO-4-ACETAMIDOANISOLE;2-AMINO-4-ACETYLAMINOANISOLE;3-AMINO-4-METHOXY ACETANILIDE;3'-AMINO-4'-METHOXYACETANILIDE;3-AMINO-4-METHOXYACETANILINE;3'-AMINO-4'-METHOXYACETOANILIDE;4-ACETOAMINO-2-AMINO METHOXYBENZENE;4-ACETAMINO-2-AMINOANISOLE
• CAS NO: 6375-47-9
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.2
• EINECS: 228-938-8
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 6375-47-9.mol

Chemical Properties

• Melting Point: 109°C
• Boiling Point: 313.03°C (rough estimate)
• Flash Point: 199.2 °C
• Appearance: /
• Density: 1.1819 (rough estimate)
• Vapor Pressure: 2.46E-15mmHg at 25°C
• Refractive Index: 1.5373 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 14.23±0.70(Predicted)
• CAS DataBase Reference: 3'-Amino-4'-methoxyacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Amino-4'-methoxyacetanilide(6375-47-9)
• EPA Substance Registry System: 3'-Amino-4'-methoxyacetanilide(6375-47-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 6375-47-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3'-Amino-4'-methoxyacetanilide is used as an analgesic and antipyretic agent for its ability to relieve mild to moderate pain and reduce fever. It is particularly effective in treating conditions such as headaches, muscle aches, arthritis, and colds.
Used in Pain Management:
3'-Amino-4'-methoxyacetanilide is utilized as a pain management tool due to its ability to inhibit the production of prostaglandins, which are responsible for promoting pain and fever in the body.
Used in Over-the-Counter Medications:
3'-Amino-4'-methoxyacetanilide is a key ingredient in various over-the-counter medications, making it accessible for individuals seeking relief from common ailments without a prescription.
Used in Healthcare Settings:
In healthcare settings, 3'-Amino-4'-methoxyacetanilide is used as a medication to manage pain and fever, ensuring patient comfort and facilitating recovery from various conditions.
It is crucial to note that while 3'-Amino-4'-methoxyacetanilide is effective for its intended uses, it must be used responsibly and as directed by a healthcare professional to avoid potential liver damage and other serious complications.

InChI:InChI=1/C22H19NO5/c1-27-19-11-13(7-9-17(19)24)22(14-8-10-18(25)20(12-14)28-2)15-5-3-4-6-16(15)23-21(22)26/h3-12,24-25H,1-2H3,(H,23,26)

Synthetic route

2-nitro-4-acetylamino-anisole (50651-39-3) + formic acid hydrazide (624-84-0) → 3-amino-4-methoxyacetanilide (6375-47-9)

Conditions	Yield
With palladium on activated charcoal In methanol at 20℃;	99.5%

2,4-Diaminoanisole (615-05-4) + acetic anhydride (108-24-7) → 3-amino-4-methoxyacetanilide (6375-47-9)

Conditions	Yield
With sodium carbonate In methanol at 5℃; for 0.00416667h; Temperature; Concentration; Reagent/catalyst; Time;	99%
With sodium carbonate In methanol at 5℃; Reagent/catalyst; Temperature;	98.6%
In methanol at 0 - 5℃; for 1.16667h; Solvent; Large scale;	98.5%

→ 3-amino-4-methoxyacetanilide

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 50℃; under 4500.45 Torr; for 0.416667h;	98.1%
With hydrogen In methanol at 60℃; under 11251.1 Torr;	96.52%
With hydrogen at 80℃; under 7500.75 Torr; Large scale;	96.52%

→ 3-amino-4-methoxyacetanilide

Conditions	Yield
Multi-step reaction with 3 steps 1: PEG4000 / 60 °C / Large scale 2: hydrogen / methanol / 60 °C / 4500.45 Torr / pH 9 3: sodium carbonate / methanol / 5 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / 3 h / 60 °C 2: PdCu/graphene double-metal catalyst / 0.58 h / 60 °C / 7500.75 Torr 3: ammonium bicarbonate / methanol / -5 - 5 °C 4: palladium on activated charcoal; hydrogen / methanol / 0.42 h / 50 °C / 4500.45 Torr View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 35 - 65 °C 2: sodium disulfide / water / 80 °C 3: acetic acid; triethylamine / 2.5 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: PEG2000 / methanol / 60 °C 2: palladium on activated charcoal; formic acid hydrazide / methanol 3: magnesium oxide / methanol / -5 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: PEG4000 (polyethyleneglycol 4000) / 60 °C 2: hydrogen / methanol / 40 °C / 30003 Torr / Autoclave 3: sodium carbonate / methanol / -5 - 5 °C View Scheme

→ 3-amino-4-methoxyacetanilide

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon / methanol / 30 - 40 °C / 375.04 - 1500.15 Torr / Inert atmosphere 2: sulfuric acid; nitric acid / 3 h 3: palladium 10% on activated carbon / methanol / 30 - 40 °C / 375.04 - 1500.15 Torr / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: hydrogen / methanol / 80 °C / 9000.9 Torr / Large scale 2: 8 h / 190 °C 3: nitric acid; sulfuric acid / water / 12 h / 0 - 5 °C 4: hydrogen / methanol / 60 °C / 11251.1 Torr View Scheme
Multi-step reaction with 4 steps 1: hydrogen; / methanol / 100 °C / 15001.5 Torr / Large scale 2: 200 °C / Large scale 3: sulfuric acid; nitric acid / 5 °C / Large scale 4: hydrogen; / 80 °C / 7500.75 Torr / Large scale View Scheme

Upstream product

• 50651-39-3 2-nitro-4-acetylamino-anisole 
• 615-05-4 2,4-Diaminoanisole 
• 108-24-7 acetic anhydride 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 100-17-4 para-methoxynitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 577-72-0 4-methoxy-3-nitroaniline 
• 104-94-9 4-methoxy-aniline 
• 624-84-0 formic acid hydrazide 
• 51-28-5 2,4-Dinitrophenol 
• 119-27-7 2,4-dinitroanisole 

Downstream Products

• 19433-93-3 3-acetylamino-6-methoxy-N,N-diethylaniline 
• 51868-45-2 3-(N,N-diprop-2-enamino)-4-methoxyacetanilide 
• 4513-20-6 3-N,N-diethylamino-4-methoxy-aniline 
• 108094-73-1 C₁₉H₁₈N₄O₁₁S₃ 
• 722550-78-9 N-[3-(3-benzoyl-thioureido)-4-methoxy-phenyl]-acetamide 

Relevant articles and documents

Hydrogenation of 3-nitro-4-methoxy-acetylaniline with H2 to 3-amino-4-methoxy-acetylaniline catalyzed by bimetallic copper/nickel nanoparticles

Monometallic Cu, monometallic Ni, and bimetallic CuxNiy nanoparticles were prepared by a wet chemical reduction method. A Cu-Ni alloy phase was formed in the bimetallic CuxNiy nanoparticles. The bimetallic CuxNiy nanoparticles exhibited higher catalytic activity for the hydrogenation of 3-nitro-4-methoxy-acetylaniline (NMA) to 3-amino-4-methoxy-acetylaniline (AMA) with H2 than the sole Ni nanoparticles, which was ascribed to the effect of the Cu-Ni alloy phase. When the reaction was catalyzed over the bimetallic Cu0.7Ni0.3 catalyst at 140 °C for 2 h, the AMA selectivity was 99.4% when the NMA conversion was 95.7%. The reaction activation energy for NMA hydrogenation was 19.74 kJ mol-1.

Synthesis process of 2-amino-4-acetylaminoanisole

The invention discloses a synthesis process of 2-amino-4-acetylaminoanisole. The process includes: taking 2, 4-dinitroanisole as the raw material, performing hydrogenation to obtain 2, 4-diaminoanisole, complexing the 2-amino of 2, 4-diaminoanisole with an acidification reagent, then carrying out acylation reaction with an acetylation reagent to obtain 2-amino-4-acetylaminoanisole. The synthesis method provided by the invention not only effectively reduces the oxidation of diamino and secondary acylation of amino, improves the purity and yield of 2-amino-4-acetylaminoanisole, but also recyclesthe catalyst and methanol, and effectively utilizes the hydrogenation reaction heat, meets the requirements of clean production, and can be used for industrial production.

2 - Amino - 4 - acetamido anisole novel synthesis process (by machine translation)

The present invention provides a novel 2 - amino - 4 - acetamido anisole synthesis process, the usage of palladium bi-metal catalysts and the palladium/carbon catalyst to replace Rany - Ni catalyst, to the anisole on the nitro-selective catalytic hydrogenation, which not only reduces use Rany - Ni catalyst of post-industrial risks, while at the same time, the resulting 2 - amino - 4 - acetyl anisole purity higher, greater yield. (by machine translation)

Synthesis process of 4-acetamino-2-aminoanisol

The invention belongs to the field of fine chemical engineering, and discloses a synthesis process of 4-acetamino-2-aminoanisol. The synthesis method comprises the following steps: step one, adding 0.25 mol of 2,4-dinitrochlorobenzene and 100 ml of methyl alcohol, carrying out heating to 35-45 DEG C, adding a sodium hydroxide solution with a mass fraction of 20% with a decreasing speed, carrying out heating to 55-65 DEG C, carrying out filtering, diluting the filter cake with water, and carrying out drying under reduced pressure to obtain 2,4-nitroanisole; step two, preparing 200 ml of a sodium disulfide solution with a concentration of 20%, adding 0.25 mol of the 2,4-dinitroanisole, carrying out heating to a reflux temperature, then carrying out cooling to 80 DEG C, carrying out standing,washing a filter cake by using cold water, and carrying out drying under reduced pressure to obtain 2,4-diaminophenyl ether; and step three, adding 0.25 mol of 2,4-diaminoanisole, 50 ml of acetic acid and 0.1 mol of a catalyst, carrying out ice bath, adding 0.25 mol of acetic anhydride, adding 125 ml of ice water, carrying out filtering, washing a filter cake with a solution of sodium dithionite,and carrying out drying under reduced pressure to obtain the 4-acetamino-2-aminoanisol. The invention aims at providing the synthesis process of 4-acetamino-2-aminoanisol, and the synthesis method has the advantages of high recovery rate, simple process and low cost.

Process for synthesizing 2-amino-4-acetylaminoanisole

The invention discloses a process for synthesizing 2-amino-4-acetylaminoanisole. The process comprises the steps of preparing 2,4-dinitroanisole from 2,4-dinitrochlorobenzene, which serves as a raw material, in methanol, in the presence of sodium hydroxide or potassium hydroxide, carrying out reduction in the presence of action of Pd/C catalyst by taking hydrazine monoformate as a hydrogen sourceso as to prepare a 2,4-diaminoanisole-methanol solution, and then, subjecting 2,4-diaminoanisole and acetic anhydride to a partial acylation reaction in the presence of an acid binding agent, therebypreparing the 2-amino-4-acetylaminoanisole. According to the process disclosed by the invention, the energy consumption is low, the cost is low, the volume of solid waste and waste liquid is small, the process is environmentally friendly, the operation is simple, the reaction conditions are mild, the industrial safety coefficient is big, the total yield of a target compound is 85% or more (by initial reactants), the HPLC purity is 99.0% or more, and the target compound is high in yield and good in quality, so that the process is more applicable to industrial production.

Synthesis process of 2-amidogen-4-acetamido anisole

The invention discloses a synthesis process of 2-amidogen-4-acetamido anisole. The synthesis process of the 2-amidogen-4-acetamido anisole comprises the steps of adopting p-methoxyaniline as a raw material, carrying out partial acylation reaction on the p-methoxyaniline and acetic anhydride, and preparing to obtain p-acetamido anisole; then carrying out nitration reaction, carrying out one-pot method'reaction to obtain 2-nitro-4-acetamido anisole, and under the action of a Pd/C catalyst, reducing the 2-nitro-4-acetamido anisole by adopting hydrazine monoformate as a hydrogen source to preparethe 2-amidogen-4-acetamido anisole. The synthesis process provided by the invention is low in energy consumption, low in cost, less in solid wastes and waste liquids, green and environmentally friendly, simple to operate, mild in reaction conditions, and high in industrial safety coefficient, the total yield of the target compound is 85 percent or above (on the basis of an initial reaction raw material), the HPLC (High Performance Liquid Chromatography) purity is 99.0 percent or above, the target compound is high in yield and good in quality, and the synthesis process is more suitable for industrial production.

Synthesis method for disperse dye intermediate

The invention discloses a synthesis method for a disperse dye intermediate. The synthesis method comprises the following steps: preparing 2,4-diaminophenol through reduction reaction of 2,4-dinitrophenol and hydrogen gas; enabling 2,4-diaminophenol and iodomethane to generate etherification reaction under action of a catalyst tributyl methyl ammonium carbonate to prepare 2,4-diaminoanisole; and enabling 2,4-diaminoanisole and acetic anhydride to generate acylation reaction to prepare a target product 3-amino-4-methoxya-cetanilide. Compared with a 2,4-diaminoanisole hydrogenation reduction process, the 2,4-dinitrophenol hydrogenation reduction process is adopted, so that the conversation rate is high and the side reactions are fewer.

A 2 - amino - 4 - acetyl amino methyl ether synthesis method (by machine translation)

The invention discloses a 2 - amino - 4 - acetyl amino methyl ether synthesis method. The synthetic method comprises the following steps: (1) in the presence of a catalyst A, to nitroanisole with hydrogen by a catalytic hydrogenation reduction reaction to obtain the amino anisole; (2) P a the fuel to the acetylation reaction acetyl amino anisole; (3) to the acetaminophen a fuel for nitration reaction to obtain the 2 - nitro - 4 - acetamido anisole; (4) in the presence of a catalyst B, 2 - nitro - 4 - acetyl amino methyl ether with hydrogen by secondary catalytic hydrogenation reduction reaction. This invention adopts the first acylation, re-nitration, reduction method for synthesis of 2 - amino - 4 - acetyl amino methyl ether, avoids the traditional directional acylate raw material is easy to oxidation in the process, a plurality of side reaction, the product is hard to separate, the problem of low purity, the method of the invention the synthetic product purity can be up to 99.5% -99.8%. (by machine translation)

Industrial production method for 2-amino-4-acetamidoanisole

The invention discloses an industrial production method for 2-amino-4-acetamidoanisole. The industrial production method comprises the following steps: (1) allowing paranitroanisole and hydrogen to undergo a catalytic hydrogenation reduction reaction in the presence of a catalyst A so as to obtain p-aminoanisole; (2) allowing the p-aminoanisole to undergo an acetylation reaction so as to obtain p-acetamidoanisole; (3) allowing the p-acetamidoanisole to undergo a nitration reaction so as to obtain 2-nitro-4-acetamidoanisole; and (4) allowing 2-nitro-4-acetamidoanisole and hydrogen to undergo two catalytic hydrogenation reduction reactions in the presence of a catalyst B so as to obtain the 2-amino-4-acetamidoanisole. The production method provided by the invention has the characteristics oflow production cost, high reaction selectivity, simple separation process, high product purity, no three wastes in the process of production, recyclability and continuous large-scale industrial production, and solves the disadvantages of high separation cost, low product purity, and large discharge amount and difficult treatment of three wastes in the prior art.

Method for continuous production of 2-amino-4-acetaminoanisole

The invention discloses a method for continuous production of 2-amino-4-acetaminoanisole and belongs to preparation of organic compounds. According to the method, 2,4-dinitrobenzene methyl ether is used as a raw material, and the 2-amino-4-acetaminoanisole is obtained through hydrogenation reduction and selective acylation. The method adopts a continuous flow process, the phenomenon that the 2-amino-4-acetaminoanisole is in contact with air and accordingly is oxidized is avoided through strict control of raw material proportion, standing time and reaction temperature, the selective acylate 2-amino-4-acetaminoanisole is obtained at high yield, the yield is up to 99%, and the purity is up to 99.9%.