4-(4-Aminophenoxy)-N-methylpicolinamide supplier

Name
4-(4-Aminophenoxy)-N-methylpicolinamide
EINECS 608-211-5
CAS No. 284462-37-9
Article Data70
CAS DataBase
Density 1.241 g/cm³
Solubility
Melting Point 110-112 °C
Formula C₁₃H₁₃N₃O₂
Boiling Point 476.8 °C at 760 mmHg
Molecular Weight 243.265
Flash Point 242.2 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Pyridinecarboxamide,4-(4-aminophenoxy)-N-methyl-;4-(4-Aminophenoxy)-N-methyl-2-pyridinecarboxamide;4-[[2-(N-Methylcarbamoyl)-4-pyridyl]oxy]anilin;[4-(4-Aminophenoxy-2-pyridyl)]-2-methylcarboxamide;
PSA 77.24000
LogP 2.78780

Synthetic route

: 123-30-8
4-amino-phenol

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 25℃; for 1h;	97%
Stage #1: 4-amino-phenol With potassium hydroxide for 0.166667h; Stage #2: 4-chloro-N-methylpicolinamide for 1.5h;	97.3%
With 18-crown-6 ether In acetonitrile for 1.5h; Reagent/catalyst; Solvent; Temperature; Reflux;	92.5%

: 864272-34-4
4-(4-nitro)benzyloxy-2-carbonylmethylaminopyridine

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
With hydrogen; nickel In tetrahydrofuran; methanol at 20℃; Product distribution / selectivity;	97%
With palladium 10% on activated carbon; hydrogen In methanol at 35℃; under 2068.65 Torr; for 2h;	95%
With palladium 10% on activated carbon; hydrogen In methanol at 40 - 50℃; under 7500.75 Torr; Solvent; Autoclave;	92.5%
Stage #1: 4-(4-nitro)benzyloxy-2-carbonylmethylaminopyridine With iron(III) chloride hexahydrate; pyrographite In ethanol at 90℃; for 0.5h; Sonication; Stage #2: With hydrazine hydrate In ethanol Sonication;	70%
With ammonia; tetra(n-butyl)ammonium hydrogensulfate; iron	20.1 g

: 100-02-7
4-nitro-phenol

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-nitro-phenol; 4-chloro-N-methylpicolinamide With potassium carbonate for 4h; Reflux; Stage #2: With iron(III) chloride; hydrazine hydrate; FeCl3/C In ethanol for 3h; Concentration; Reflux;	94.6%
Stage #1: 4-nitro-phenol With potassium hydroxide for 0.166667h; Heating; Green chemistry; Stage #2: 4-chloro-N-methylpicolinamide for 1.5h; Green chemistry; Stage #3: With iron(III) chloride; pyrographite; hydrazine hydrate In ethanol; 1,2-dichloro-ethane for 3h; Reflux; Green chemistry;	94.5%

: C12H9ClN2O2

: 74-89-5
methylamine

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at -5 - 10℃; for 1.5h; Large scale;	84.1%

: 73771-11-6
4-chloropyridine-2-carbohydrazide

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: 4-chloropyridine-2-carbohydrazide With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;	80%

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-amino-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 4-chloro-N-methylpicolinamide With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	71%
With potassium tert-butylate; potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 10h; Product distribution / selectivity;
Multi-step reaction with 2 steps 1: ethyl acetate 2: ammonia; iron; tetra(n-butyl)ammonium hydrogensulfate View Scheme

: 114780-06-2
4-chloro-N,N-dimethylpyridine-2-carboxamide

: 123-30-8
4-amino-phenol

: 220000-87-3
4-chloro-N-methylpicolinamide

A: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B: 284462-86-8
4-(4-aminophenoxy)-N,N-dimethylpicolinamide

Conditions

Conditions	Yield
Stage #1: 4-amino-phenol With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-chloro-N,N-dimethylpyridine-2-carboxamide; 4-chloro-N-methylpicolinamide With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;	A 70% B 69%

...Expand

: 284462-78-8
4-(3-aminophenoxy)-N-methylpicolinamide

: 32315-10-9
bis(trichloromethyl) carbonate

: 67291-63-8
2-amino-3-methoxynaphthalene

A: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B: 5-tert-Butyl-2-(2,5-dimethylpyrrolyl)-aniline

...Expand

: 284462-56-2
3-(4-aminophenoxy)-N-methylbenzamide

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

of4-aminophenol: of4-aminophenol

: 220000-87-3
4-chloro-N-methylpicolinamide

A: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B of4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline: of4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline

Conditions

Conditions	Yield
With potassium tert-butylate; potassium carbonate In N,N-dimethyl-formamide

...Expand

: 98-98-6
2-Picolinic acid

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 17.5 h / 50 °C / Inert atmosphere; Reflux 2.1: tetrahydrofuran; methanol / 0 - 20 °C 3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C 3.2: 6 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / 16 h / 72 °C 2: 5 h / 3 °C 3: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 50 °C / Inert atmosphere; Reflux 2.1: tetrahydrofuran; methanol / 2 h / 0 - 20 °C 3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C 3.2: 6 h / 80 °C / Inert atmosphere View Scheme

: 53750-66-6
4-chloro-pyridine-2-carbonyl chloride

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; methanol / 0 - 20 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 6 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; methanol / 2 h / 0 - 20 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 6 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: 2 h / 30 °C 2.1: tetrahydrofuran; methanol / 3 h / 2 - 20 °C 3.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 10 h / 80 - 85 °C View Scheme

: 4-chloro-2-pyridine carboxylic acid chloride hydrochloride

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 h / 3 °C 2: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; methanol / 4 h / 0 - 3 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 8 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 16.42 h / 0 - 20 °C / Inert atmosphere 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2.02 h / Inert atmosphere 2.2: 4 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; methanol / 4 h / 0 - 3 °C 2.1: potassium tert-butylate / DMF (N,N-dimethyl-formamide) / 2 h / 20 °C 2.2: 8 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: water; tetrahydrofuran 2: sodium hydride / dimethyl sulfoxide / 3 h / 100 °C View Scheme

: 24484-93-3
4-Chloro-pyridine-2-carboxylic acid methyl ester

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; methanol / 3 h / 2 - 20 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 10 h / 80 - 85 °C View Scheme
Multi-step reaction with 2 steps 1: water / 3 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 100 °C View Scheme
Multi-step reaction with 2 steps 1: water; tetrahydrofuran / 3 h / 20 °C 2: potassium tert-butylate / N,N-dimethyl-formamide / 3 h / 100 °C View Scheme

: 99586-65-9
4-chloropicolinamide

: 123-30-8
4-amino-phenol

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-amino-phenol With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: 4-chloropicolinamide With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;

: 1012058-77-3
4‐(4‐aminophenoxy)‐2‐pyridine carboxylic acid

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / chloroform / 1.5 h / Reflux; Large scale 2: potassium carbonate / water; N,N-dimethyl-formamide / 1.5 h / -5 - 10 °C / Large scale View Scheme

: 62150-45-2
4-bromo-2-cyanopyridine

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; water / 5.5 h / Reflux; Large scale 2: thionyl chloride / chloroform / 1.5 h / Reflux; Large scale 3: potassium carbonate / water; N,N-dimethyl-formamide / 1.5 h / -5 - 10 °C / Large scale View Scheme

: 123-30-8
4-amino-phenol

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; water / 5.5 h / Reflux; Large scale 2: thionyl chloride / chloroform / 1.5 h / Reflux; Large scale 3: potassium carbonate / water; N,N-dimethyl-formamide / 1.5 h / -5 - 10 °C / Large scale View Scheme

: 284461-73-0
sorafenib

A: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B: 123-30-8
4-amino-phenol

Conditions

Conditions	Yield
With hydrogenchloride; water; sodium chloride at 0℃; for 3h; pH=1.5; pH-value;

: 5470-22-4
4-chloropicolinic acid

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 15.5 h / 0 - 20 °C / Inert atmosphere 2.1: tetrahydrofuran / 16.42 h / 0 - 20 °C / Inert atmosphere 3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2.02 h / Inert atmosphere 3.2: 4 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol; water / 4 h / 120 °C 2: ethyl acetate 3: ammonia; iron; tetra(n-butyl)ammonium hydrogensulfate View Scheme

: 6144-78-1
N-methylpyridine-2-carboxamide

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: fluorine; sulfuric acid / 25 °C 2: caesium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 35 °C / 2068.65 Torr View Scheme

: 64064-56-8
ethyl 4-chloropyridine-2-carboxylate

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: chlorobenzene / 4 h / 130 °C / UV-irradiation 2.1: ethanol; sodium hydroxide / 1 h / 20 °C 3.1: thionyl chloride / 0.17 h / 85 °C / Sonication 4.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice 4.2: 0.5 h / Cooling with ice 5.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication 5.2: Sonication View Scheme

Yield

Multi-step reaction with 5 steps
1.1: chlorobenzene / 4 h / 130 °C / UV-irradiation
2.1: ethanol; sodium hydroxide / 1 h / 20 °C
3.1: thionyl chloride / 0.17 h / 85 °C / Sonication
4.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice
4.2: 0.5 h / Cooling with ice
5.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication
5.2: Sonication
View Scheme

: ethyl 4-(4-nitrophenoxy)picolinate

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethanol; sodium hydroxide / 1 h / 20 °C 2.1: thionyl chloride / 0.17 h / 85 °C / Sonication 3.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice 3.2: 0.5 h / Cooling with ice 4.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication 4.2: Sonication View Scheme

: 4-(4-nitrophenoxy)picolinic acid

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 0.17 h / 85 °C / Sonication 2.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice 2.2: 0.5 h / Cooling with ice 3.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication 3.2: Sonication View Scheme

: 4-(4-nitrophenoxy)pyridine-2-carbonyl chloride

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice 1.2: 0.5 h / Cooling with ice 2.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication 2.2: Sonication View Scheme

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: (4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With 1-Methylpyrrolidine In dichloromethane at 30℃; for 24h; Solvent; Temperature;	97.6%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 115029-23-7
2-fluoro-5-(trifluoromethyl)benzoic acid

: 1313019-74-7
4-(4-(2-fluoro-5(trifluoromethyl)benzamido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
Stage #1: 2-fluoro-5-(trifluoromethyl)benzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.516667h; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In N,N-dimethyl-formamide for 12h;	97%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 404-71-7
1-fluoro-3-isocyanatobenzene

: 4-(4-(3-(3-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In dichloromethane for 48h;	97%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 327-78-6
4-chloro-3-(trifluoromethyl)phenyl isocyanate

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With zirconia grinding balls In acetonitrile for 4h; Milling;	96%
In ethyl acetate at 20 - 30℃; Large scale;	94.2%
In dichloromethane	93%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 104-15-4
toluene-4-sulfonic acid

: 327-78-6
4-chloro-3-(trifluoromethyl)phenyl isocyanate

: sorafenib tosylate

Conditions

Conditions	Yield
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In ethyl acetate at 40 - 71℃; for 0.5h; Stage #2: toluene-4-sulfonic acid In water; ethyl acetate at 71℃; for 0.666667h; Product distribution / selectivity;	96%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In butanone at 20 - 85℃; Stage #2: toluene-4-sulfonic acid In butanone at 20℃;	88%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In tetrahydrofuran at 25 - 64℃; for 0.5h; Stage #2: toluene-4-sulfonic acid In tetrahydrofuran at 64℃; Product distribution / selectivity;	81.6%

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1195-45-5
para-fluorophenyl isocyanate

: 1285533-80-3
4-[4-[[[[4-fluorophenyl]amino]carbonyl]amino]phenoxy]-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
In dichloromethane for 48h;	96%
In acetone at 20 - 40℃;

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1737-36-6
4-chloro-3-(trifluoromethyl)benzoic acid

: 530-62-1
1,1'-carbonyldiimidazole

: 4-(4-(4-chloro-3-(trifluoromethyl)phenylamido)phenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 1,1'-carbonyldiimidazole In tetrahydrofuran at 45℃; for 3h; Inert atmosphere; Enzymatic reaction; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In tetrahydrofuran at 20℃; for 2h;	96%

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 69922-27-6
1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene

: 847054-10-8
4-(4-(3-(2-fluoro-5-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpyridine-2-carboxamide

Conditions

Conditions	Yield
In dichloromethane for 72h;	96%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 16744-98-2
1-Fluoro-2-isocyanato-benzene

: 4-(4-(3-(2-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In dichloromethane for 48h;	96%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1187086-96-9
N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
In chlorobenzene at 70 - 75℃; for 0.25h; Product distribution / selectivity;	95%
In ethyl acetate at 20 - 50℃; for 2.75h;	77%
With potassium carbonate In dichloromethane for 8h; Milling;	72%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1548-13-6
p-trifluoromethyl-phenylisocyanate

: N-methyl-4-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenoxy)pyridine-2-carboxamide

Conditions

Conditions	Yield
In dichloromethane for 48h;	95%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 2251-65-2
3-(Trifluoromethyl)benzoyl chloride

: N-methyl-4-(4-(3-(trifluoromethyl)benzamido)phenoxy)picolinamide

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;	95%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 3-(Trifluoromethyl)benzoyl chloride With pyridine In dichloromethane for 14h; Inert atmosphere; Stage #2: With pyridine	74%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 39718-32-6
2,5-difluorophenyl isocyanate

: 4-(4-(3-(2,5-difluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In dichloromethane for 24h;	94%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 329-15-7
4-trifluoromethyl-phenyl acetyl chloride

: 1125780-43-9
N-methyl-4-(4-(4-(trifluoromethyl)benzamido)phenoxy)picolinamide

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;	93.2%
With pyridine In tetrahydrofuran at 20℃; for 2h;

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 2,6-difluorophenyl isocyanate

: 4-(4-(3-(2,6-difluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In dichloromethane for 48h;	93%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 15863-41-9
1-isothiocyanato-4-(methylthio)benzene

: N-methyl-4-(4-(3-(4-(methylthio)phenyl)thioureido)phenoxy)picolinamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	93%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1737-36-6
4-chloro-3-(trifluoromethyl)benzoic acid

: 2,2,2,-trichloroethoxycarbonyl azide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 2,2,2,-trichloroethoxycarbonyl azide With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Curtius Rearrangement; Inert atmosphere; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	93%

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1544-68-9
4-fluorophenyl isothiocyanate

: 1229611-42-0
4-(4-(3-(4-fluorophenyl)thioureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	92%
In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	70.3%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 3529-82-6
3-nitrophenyl isothiocyanate

: N-methyl-4-(4-(3-(3-nitrophenyl)thioureido)phenoxy)picolinamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	92%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 3137-84-6
3-ethoxycarbonylphenyl isothiocyanate

: ethyl 3-(3-(4-((2-(methylcarbamoyl)pyridin-4-yl)oxy)phenyl)thioureido)benzoate

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	92%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 19241-24-8
4-(tert-butylbenzyl)isothiocyanate

: 4-(4-(3-(4-(tert-butyl)phenyl)thioureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	92%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 312-94-7
2-trifluoromethylbenzoyl chloride

: N-methyl-4-(4-(2-(trifluoromethyl)benzamido)phenoxy)picolinamide

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;	92%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 530-62-1
1,1'-carbonyldiimidazole

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane Inert atmosphere;	91%
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 25 - 35℃; for 18h; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane at 25 - 35℃; for 48.75h;	90 g

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 103-72-0
phenyl isothiocyanate

: N-methyl-4-(4-(3-phenylthioureido)phenoxy)picolinamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	91%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1985-12-2
4-Bromophenyl isothiocyanate

: 4-(4-(3-(4-bromophenyl)thioureido)phenoxy)-N-methylpicolinamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	91%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 41513-02-4
4-bromo-3-(trifluoromethyl)phenyl isocyanate

: 4-{4-[({[4-bromo-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methyl-2-pyridine carboxamide

Conditions

Conditions	Yield
In dichloromethane	90%
In dichloromethane	90%
In dichloromethane	90%
In dichloromethane	90%
In dichloromethane at 0 - 20℃; for 16h;	90%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1012058-77-3
4‐(4‐aminophenoxy)‐2‐pyridine carboxylic acid

Conditions

Conditions	Yield
Reflux; Alkaline conditions;	90%
With potassium carbonate In water at 100℃; for 2h;	90%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With potassium hydroxide; water at 100℃; for 2h; Stage #2: With water pH=5;	80%
With water; potassium hydroxide at 100℃;	18.9 g

4-(4-Aminophenoxy)-N-methylpicolinamide Chemical Properties

Molecular structure of 4-(4-Aminophenoxy)-N-methylpicolinamide (CAS NO.284462-37-9) is:

Product Name: 4-(4-Aminophenoxy)-N-methylpicolinamide
CAS Registry Number: 284462-37-9
Systematic Name: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
Empirical Formula: C₁₃H₁₃N₃O₂
Molecular Weight: 243.2612
Melting Point: 110-112°C
Index of Refraction: 1.618
Molar Refractivity: 68.64 cm³
Molar Volume: 195.8 cm³
Surface Tension: 54.2 dyne/cm
Density: 1.241 g/cm³
Flash Point: 242.2 °C
Enthalpy of Vaporization: 74.06 kJ/mol
Boiling Point: 476.8 °C at 760 mmHg
Vapour Pressure: 2.96E-09 mmHg at 25°C
Product Categories: Sorafinib;Aromatics Compounds;Aromatics;Bases & Related Reagents;Heterocycles;Nucleotides

4-(4-Aminophenoxy)-N-methylpicolinamide Specification

4-(4-Aminophenoxy)-N-methylpicolinamide , its cas register number is 284462-37-9. It also can be called 2-Pyridinecarboxamide,4-(4-aminophenoxy)-N-methyl- ; 4-(4-Aminophenoxy)-N-methyl-2-pyridinecarboxamide ; 4-[[2-(N-Methylcarbamoyl)-4-pyridyl]oxy]anilin ; [4-(4-Aminophenoxy-2-pyridyl)]-2-methylcarboxamide .It is a light-brown solid.

Product Name

4-(4-Aminophenoxy)-N-methylpicolinamide

Synthetic route

4-(4-Aminophenoxy)-N-methylpicolinamide Chemical Properties

4-(4-Aminophenoxy)-N-methylpicolinamide Specification

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