2486-75-1

Usage

Chemical Properties

White powder

InChI:InChI=1/C8H9NO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4H,9H2,1H3,(H,10,11)

Synthetic route

2-methyl-4-nitrobenzoic acid (1975-51-5) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol under 12001.2 Torr; Flow reactor;	98%
With hydrogenchloride; tin
With hydrogen; palladium 10% on activated carbon In methanol at 20℃; for 16h;

2-methyl-4-aminobenzonitrile (72115-06-1) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
With water; sodium hydroxide In ethylene glycol at 100℃; for 6h;	95.6%

5-nitro-3H-isobenzofuran-1-one (67081-02-1) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
With phosphorus; hydrogen iodide at 205℃;

hydrogenchloride (7647-01-0) + 2-methyl-4-nitrobenzoic acid (1975-51-5) + tin → 4-amino-2-methylbenzoic acid (2486-75-1)

hydrogenchloride (7647-01-0) + 4-acetylamino-2-methylbenzoic acid (103204-69-9) → 4-amino-2-methylbenzoic acid (2486-75-1)

2-methyl-4-aminobenzaldehyde (61594-81-8) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium formate; formic acid / 3 h / 100 °C 2: water; sodium hydroxide / ethylene glycol / 6 h / 100 °C View Scheme

1-amino-3-methylbenzene (108-44-1) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: trichlorophosphate / 6 h / 0 - 60 °C 2: hydroxylamine hydrochloride; sodium formate; formic acid / 3 h / 100 °C 3: water; sodium hydroxide / ethylene glycol / 6 h / 100 °C View Scheme

4-amino-2-methylbenzoic acid (2486-75-1) + ortho-toluoyl chloride (933-88-0) → 2-methyl-4-(2-methylbenzoylamino)benzoic acid (317374-08-6)

Conditions	Yield
With pyridine In chloroform at 0 - 40℃; for 8h; Reagent/catalyst; Solvent; Temperature;	95.6%

methanol (67-56-1) + 4-amino-2-methylbenzoic acid (2486-75-1) → methyl 4-amino-2-methylbenzoate (6933-47-7)

Conditions	Yield
With hydrogenchloride In water Reflux;	85%

4-amino-2-methylbenzoic acid (2486-75-1) + 2-(4-(8-chloroimidazo[1,2-a]pyrazin-3-yl)-2,3-difluorophenoxyl)propanenitrile → 4-((3-(4-(1-cyanoethoxyl)-2,3-difluorophenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-methylbenzoic acid

Conditions	Yield
With acetic acid In acetonitrile at 90℃; for 15h;	80.2%
With acetic acid In acetonitrile at 90℃; for 15h; Inert atmosphere;	80.2%
With acetic acid In acetonitrile at 90℃; for 15h;	80.2%
With acetic acid In acetonitrile at 90℃; for 15h; Inert atmosphere;	560 mg
With acetic acid In acetonitrile at 90℃; for 15h;	560 mg

4-amino-2-methylbenzoic acid (2486-75-1) + N,N-dimethylammonium chloride (506-59-2) → 4-amino-N,N,2-trimethylbenzamide (862470-14-2)

Conditions	Yield
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h; Inert atmosphere;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h; Inert atmosphere;

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-[(tert-butoxycarbonyl)amino]-2-methylbenzoic acid (1303931-49-8)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 2h;	73%

4-amino-2-methylbenzoic acid (2486-75-1) + 8-chloro-3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazine → 4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-ethylbenzoic acid

Conditions	Yield
With acetic acid In acetonitrile at 65℃; for 12h;	72.64%

4-amino-2-methylbenzoic acid (2486-75-1) + benzyl alcohol (100-51-6) → 4-(1,2-diphenylethylamino)-2-methylbenzoic acid (1347032-87-4)

Conditions	Yield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; sealed tube;	70%

ethanol (64-17-5) + 2-(4-hexylphenyl)-2-oxoacetaldehyde (14333-88-1) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-((1-ethoxy-2-(4-octylphenyl)-2-oxoethyl)amino)-2-methylbenzoic acid

Conditions	Yield
at 20℃;	26%

4-amino-2-methylbenzoic acid (2486-75-1) + benzyl bromide (100-39-0) → 4-Amino-2-methyl-benzoesaeure-benzylester

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	19%

ethanol (64-17-5) + 2-oxo-2-[4-(1-piperidinyl)phenyl]acetaldehyde monohydrate (1171309-72-0) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-((1-ethoxy-2-oxo-2-(4-(piperidin-1-yl)phenyl)ethyl)amino)-2-methylbenzoic acid

Conditions	Yield
at 20℃;	15%
at 20℃;

ethanol (64-17-5) + 2-(4-hexylphenyl)-2-oxoacetaldehyde (14333-88-1) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-((1-ethoxy-2-(4-hexylphenyl)-2-oxoethyl)amino)-2-methylbenzoic acid

Conditions	Yield
at 20℃;	12.6%

4-amino-2-methylbenzoic acid (2486-75-1) → 4-hydroxy-2-methylbenzoic acid (578-39-2)

Conditions	Yield
With cis-nitrous acid

4-amino-2-methylbenzoic acid (2486-75-1) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + 1-amino-3-methylbenzene (108-44-1)

Conditions	Yield
at 200℃;

4-amino-2-methylbenzoic acid (2486-75-1) + acetic anhydride (108-24-7) → 4-acetylamino-2-methylbenzoic acid (103204-69-9)

4-amino-2-methylbenzoic acid (2486-75-1) + N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (159005-71-7) → 4-Amino-N-{(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-2-methyl-benzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

4-amino-2-methylbenzoic acid (2486-75-1) + cis-nitrous acid (7782-77-6) → 4-hydroxy-2-methylbenzoic acid (578-39-2)

4-amino-2-methylbenzoic acid (2486-75-1) → 2-methyl-4-nitrobenzoic acid (1975-51-5)

Conditions	Yield
With Streptomyces thioluteus para-aminobenzoate N-oxygenase

C13H13N5O3S (840537-53-3) + 4-amino-2-methylbenzoic acid (2486-75-1) → C20H18N6O3

Conditions	Yield
With 2,6-dimethylpyridine In DMF (N,N-dimethyl-formamide) at 60℃; for 20h;

4-amino-2-methylbenzoic acid (2486-75-1) + 2-amino-benzenethiol (137-07-5) → 4-(benzo[d]thiazol-2-yl)-3-methylaniline

Conditions	Yield
With PPA at 185℃; for 5h;
With polyphosphoric acid at 125℃; for 0.583333h; Microwave irradiation;

N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1124212-41-4) + 4-amino-2-methylbenzoic acid (2486-75-1) → 3-((4-(4-amino-2-methylbenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (1124213-60-0)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃;
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃; for 2h;

4-amino-2-methylbenzoic acid (2486-75-1) → C16H13NO3 (1314003-50-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C 2: sodium hydrogencarbonate / dichloromethane; toluene; water / 0.75 h / 5 - 20 °C View Scheme

4-amino-2-methylbenzoic acid (2486-75-1) → C31H36N2O4 (1314003-51-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C 2.1: sodium hydrogencarbonate / dichloromethane; toluene; water / 0.75 h / 5 - 20 °C 3.1: sodium hydrogencarbonate / chloroform; water 3.2: 20 h / 58 °C View Scheme

Upstream product

• 67081-02-1 5-nitro-3H-isobenzofuran-1-one 
• 1975-51-5 2-methyl-4-nitrobenzoic acid 
• 99-51-4 4-nitro-o-xylene 
• 95-47-6 o-xylene 
• 108-44-1 1-amino-3-methylbenzene 
• 61594-81-8 4-amino-2-methylbenzaldehyde 
• 72115-06-1 4-amino-2-methylbenzonitrile 
• 7647-01-0 hydrogenchloride 
• 103204-69-9 4-acetylamino-2-methylbenzoic acid 

Downstream Products

• 103204-69-9 4-acetylamino-2-methylbenzoic acid 
• 1975-51-5 2-methyl-4-nitrobenzoic acid 
• 1124213-60-0 3-((4-(4-amino-2-methylbenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide 
• 1347032-87-4 4-(1,2-diphenylethylamino)-2-methylbenzoic acid 
• 1124213-58-6 N-tert-butyl-3-((4-(2-methyl-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)benzamide 
• 317374-08-6 2-methyl-4-(2-methylbenzoylamino)benzoic acid 
• 1303931-49-8 4-[(tert-butoxycarbonyl)amino]-2-methylbenzoic acid 

Relevant academic research and scientific papers

Cyhalofop-containing pesticide composition and application thereof

The invention discloses a pesticide composition containing cyhalofop-butyl and application thereof, belongs to the technical field of pesticide preparation and comprises 10 - 20 parts of cyhalofop-butyl. Tetramethyl chloride 3-5 parts, synergistic microcapsule 8-13 parts, wetting agent 1.5 - 4.5 parts, dispersing agent 1-3 parts, defoaming agent 0.5 - 1.5 parts and water 40 - 50 parts. When the water in the soil is less, the weed is absorbed by the chitosan so as to accelerate the absorption of A the synergic microcapsule and the cyhalofop-butyl ester, so that the pesticide composition is greatly reduced per mu.

A [...] intermediate 2 - methyl - 4 - N - (2 - methyl benzoyl) benzoic acid

The invention relates to a [...] intermediate 2 - methyl - 4 - N - (2 - methyl benzoyl) benzoic acid for the preparation of the new method, the method to 3 - methylaniline as the starting material, acetate acylation, cyano, cyano hydrolysis, the amidation reaction to obtain the intermediate 2 - methyl - 4 - N - (2 - methyl benzoyl) benzoic acid. The material of the invention is easy to obtain, mild reaction conditions, high yield, does not need special equipment, without the use of highly toxic or an expensive reagent, low cost, convenient to industrial production.

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

QUATERNARY AMMONIUM SALT COMPOUNDS

[Problem] The object of the present invention is to provide a novel compound having 132 adrenergic receptor agonist activity and muscarinic receptor antagonist activity. [Means for Solving the Problem] The present invention is a quaternary ammonium salt compounds represented by formula (I), or a pharmaceutically acceptable salt thereof, with superior β32 adrenergic receptor agonist activity and muscarinic receptor antagonist activity.