2-chloro-3-nitro-4-methylpyridine
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride In diethyl ether for 0.333333h; Ambient temperature; | 98% |
Stage #1: 2-chloro-3-nitro-4-methylpyridine With iron; acetic acid at 70 - 80℃; Stage #2: With sodium carbonate In water pH=8.0 - 8.5; Product distribution / selectivity; | 90.79% |
Stage #1: 2-chloro-3-nitro-4-methylpyridine With hydrogenchloride In methanol; water at 65℃; Stage #2: With iron In methanol; water at 65℃; Product distribution / selectivity; | 90.1% |
2-chloro-4-methyl-3-pyridinecarboxamide
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With sodium hypobromide; bromine; sodium hydroxide In water at 65 - 75℃; for 4h; Hofmann Rearrangement; | 98% |
With bromine; sodium hydroxide In water at 0 - 20℃; for 2h; | 97% |
With bromine; sodium hydroxide In water; toluene at 0 - 60℃; | 96.9% |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Stage #1: 4-methylpiperidin-3-one With hydrogenchloride; dihydrogen peroxide In chloroform; water at 30 - 40℃; for 5h; Green chemistry; Stage #2: With ammonium hydroxide at 40 - 45℃; for 3h; Solvent; Reagent/catalyst; Green chemistry; | 93.3% |
3-amino-4-methylpyridine
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide at 20℃; for 0.5h; | 89% |
With hydrogenchloride; chlorine In water at 20℃; for 0.416667h; | 84% |
Stage #1: 3-amino-4-methylpyridine With hydrogenchloride In water at 40℃; Cooling with ice; Stage #2: With dihydrogen peroxide for 2h; | 83.2% |
3-nitro-4-methylpyridine
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97 percent / H2 / 5 percent Pd/C / methanol / 5 h / 20 °C / 3750.3 Torr 2: 89 percent / conc. aq. HCl; 35 percent aq. H2O2 / 0.5 h / 20 °C View Scheme |
2-chloro-4-methylnicotinoylchloride
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH3(g) / toluene / below 30 deg C 2: 93 percent / NaOH, Br2 / H2O / 1.) 5 deg C; 2.) 75 deg C, 90 min View Scheme |
ethyl 2-chloro-4-methyl-3-pyridinecarboxylate
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / NaOH / methanol; H2O / 75 °C 2: SOCl2 / toluene / 1.) 70 deg C, 1 h; 2.) reflux, 4 h 3: NH3(g) / toluene / below 30 deg C 4: 93 percent / NaOH, Br2 / H2O / 1.) 5 deg C; 2.) 75 deg C, 90 min View Scheme |
2-chloro-4-methyl-3-pyridinecarboxylic acid
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: SOCl2 / toluene / 1.) 70 deg C, 1 h; 2.) reflux, 4 h 2: NH3(g) / toluene / below 30 deg C 3: 93 percent / NaOH, Br2 / H2O / 1.) 5 deg C; 2.) 75 deg C, 90 min View Scheme |
ethyl 2-chloro-2-cyano-3-methyl-5-oxopentanoate
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 17 percent / PCl3, HCl(g) / dimethylformamide / 1.) 85 deg C; 2.) 90 deg C 2: 90 percent / NaOH / methanol; H2O / 75 °C 3: SOCl2 / toluene / 1.) 70 deg C, 1 h; 2.) reflux, 4 h 4: NH3(g) / toluene / below 30 deg C 5: 93 percent / NaOH, Br2 / H2O / 1.) 5 deg C; 2.) 75 deg C, 90 min View Scheme |
2-chloro-3-nitro-4-methylpyridine
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With sodium hydroxide; acetic acid In hydrogenchloride; water |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sulfuric acid / ethanol / 3.67 h / 20 - 50 °C 2.1: trichlorophosphate / 2 h / 35 °C / Reflux 3.1: sulfuric acid / 4 h / 50 - 105 °C 3.2: 1.5 h / 60 - 65 °C 3.3: pH 7 / Cooling with ice 4.1: sodium hypochlorite; sodium hydroxide / methanol; water / 4 h / 10 - 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sulfuric acid / ethanol / 1.17 h / 25 - 50 °C 2.1: trichlorophosphate / 2.25 h / 35 °C / Reflux 2.2: 50 - 110 °C 3.1: sodium hydroxide; sodium hypochlorite / ethanol; water / 4.17 h / 10 - 60 °C View Scheme |
2-hydroxy-4-methylpyridine-3-carbonitrile
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 2 h / 35 °C / Reflux 2.1: sulfuric acid / 4 h / 50 - 105 °C 2.2: 1.5 h / 60 - 65 °C 2.3: pH 7 / Cooling with ice 3.1: sodium hypochlorite; sodium hydroxide / methanol; water / 4 h / 10 - 60 °C View Scheme |
2-chloro-4-methyl-3-pyridinecarbonitrile
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 4 h / 50 - 105 °C 1.2: 1.5 h / 60 - 65 °C 1.3: pH 7 / Cooling with ice 2.1: sodium hypochlorite; sodium hydroxide / methanol; water / 4 h / 10 - 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sulfuric acid / 1.25 h / 40 - 105 °C 1.2: 70 - 75 °C 2.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / water / 8.25 h / 40 - 105 °C 2: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C View Scheme |
2-amino-4-methyl-3-nitropyridine
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium nitrite; sulfuric acid / water 2: trichlorophosphate / 110 °C 3: tin(II) chloride dihdyrate; hydrogenchloride / 55 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium nitrite; sulfuric acid / 4 h / 20 °C 2: trichlorophosphate / 4 h / 110 °C 3: tin(II) chloride dihdyrate; hydrogenchloride / 1 h / 50 °C View Scheme |
2-hydroxy-4-methyl-3-nitropyridine
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / 110 °C 2: tin(II) chloride dihdyrate; hydrogenchloride / 55 °C View Scheme | |
Multi-step reaction with 2 steps 1: trichlorophosphate / 4 h / 110 °C 2: tin(II) chloride dihdyrate; hydrogenchloride / 1 h / 50 °C View Scheme |
2-(4-(dimethylamino)but-3-en-2-ylidene)malononitrile
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 2 h / 50 - 55 °C 2.1: sulfuric acid / 1.25 h / 40 - 105 °C 2.2: 70 - 75 °C 3.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride / toluene / 20 - 55 °C 2: sulfuric acid / water / 8.25 h / 40 - 105 °C 3: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C View Scheme |
isopropylidenemalonodinitrile
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine; acetic anhydride / toluene / 2 h / 5 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / 2 h / 50 - 55 °C 3.1: sulfuric acid / 1.25 h / 40 - 105 °C 3.2: 70 - 75 °C 4.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: acetic anhydride / toluene / 5 - 10 °C / Inert atmosphere 1.2: 2 h / 5 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / toluene / 20 - 55 °C 3.1: sulfuric acid / water / 8.25 h / 40 - 105 °C 4.1: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C View Scheme |
picoline
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; potassium bromide / 1 h / 20 °C / Inert atmosphere 1.2: 27 h / 120 °C / Inert atmosphere 2.1: copper(II) sulfate; ammonia / methanol / 8 h / 160 °C / 3800.26 Torr / Autoclave 3.1: hydrogenchloride / water / 40 °C / Cooling with ice 3.2: 2 h View Scheme |
3-methyltetrahydro-2-furanone
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 5 h / 40 - 45 °C / Green chemistry 1.2: 4 h / 20 - 25 °C / Green chemistry 1.3: 4 h / 30 - 35 °C / 1500.15 - 2250.23 Torr / Autoclave; Green chemistry 2.1: hydrogenchloride; dihydrogen peroxide / chloroform; water / 5 h / 30 - 40 °C / Green chemistry 2.2: 3 h / 40 - 45 °C / Green chemistry View Scheme |
3-Amino-2-chloro-4-methylpyridine
Nevirapine
Conditions | Yield |
---|---|
With sodium hydride In diethylene glycol dimethyl ether at 65 - 165℃; Flow reactor; Green chemistry; | 96% |
Multi-step reaction with 2 steps 1.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 1.2: 2 h / 55 - 65 °C / Inert atmosphere 2.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 1.2: 2 h / 60 °C 2.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme |
3-Amino-2-chloro-4-methylpyridine
2-chloro-3-amino-4-methyl-6-bromopyridine
Conditions | Yield |
---|---|
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 0 - 20℃; for 1.66667h; Product distribution / selectivity; | 94% |
3-Amino-2-chloro-4-methylpyridine
N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide
Conditions | Yield |
---|---|
Stage #1: 3-Amino-2-chloro-4-methylpyridine With sodium hydride In diethylene glycol dimethyl ether at 20℃; for 0.5h; Stage #2: methyl 2-(cyclopropylamino)nicotinate In diethylene glycol dimethyl ether at 60℃; for 2h; Reagent/catalyst; | 94% |
2-Chloronicotinoyl chloride
3-Amino-2-chloro-4-methylpyridine
2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide
Conditions | Yield |
---|---|
In dichloromethane 1.) -78 deg C, 1 h, 2.) RT, 23 h; | 87% |
With pyridine In 1,4-dioxane; cyclohexane for 48h; Ambient temperature; | 65.5% |
With potassium carbonate In ethyl acetate at 75 - 80℃; for 14h; Product distribution / selectivity; |
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
3-Amino-2-chloro-4-methylpyridine
(E)-ethyl 3-(2-chloro-4-methylpyridin-3-yl-amino)-2-cyano-3-methylthioacrylate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 0.5h; microwave irradiation; | 85.2% |
With sodium hydride In N,N-dimethyl-formamide; toluene at 40 - 45℃; for 1h; | 73.5% |
3-Amino-2-chloro-4-methylpyridine
Cyclopropylamine
N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide
Conditions | Yield |
---|---|
In toluene at 125 - 130℃; under 775.743 Torr; for 21h; | 79.64% |
methanol
3-Amino-2-chloro-4-methylpyridine
2-methoxy-3-amino-4-methylpyridine
Conditions | Yield |
---|---|
With copper(l) iodide; sodium at 110℃; for 14h; Autoclave; | 78.7% |
With copper(l) iodide; sodium at 110℃; for 14h; Autoclave; | 78.7% |
3-Amino-2-chloro-4-methylpyridine
4,5-dichloro-1,2,3-dithiazolium chloride
(Z)-2-chloro-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methylpyridin-3-amine
Conditions | Yield |
---|---|
Stage #1: 3-Amino-2-chloro-4-methylpyridine; 4,5-dichloro-1,2,3-dithiazolium chloride In dichloromethane at 20℃; for 1h; Stage #2: With 2,6-dimethylpyridine In dichloromethane at 20℃; for 2h; | 60% |
Stage #1: 3-Amino-2-chloro-4-methylpyridine; 4,5-dichloro-1,2,3-dithiazolium chloride In dichloromethane for 1h; Stage #2: With pyridine for 2h; | 42% |
3-Amino-2-chloro-4-methylpyridine
2-chloro-3-iodo-4-methyl-pyridine
Conditions | Yield |
---|---|
Stage #1: 3-Amino-2-chloro-4-methylpyridine With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With potassium iodide In water at 0 - 20℃; | 58% |
Stage #1: 3-Amino-2-chloro-4-methylpyridine With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With potassium iodide In water at 0 - 20℃; | 47% |
Stage #1: 3-Amino-2-chloro-4-methylpyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: With potassium iodide In water at 0 - 20℃; for 12h; |
2-Picolinic acid
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 70℃; for 15h; | 55% |
2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamido)acetic acid
3-Amino-2-chloro-4-methylpyridine
3-bromo-N-(2-((2-chloro-4-methylpyridin-3-yl)amino)-2-oxoethyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate In acetonitrile for 2h; Reflux; | 52.6% |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With selenium; sodium tetrahydroborate; toluene-4-sulfonic acid at 50℃; for 20h; Inert atmosphere; | 51% |
3-Amino-2-chloro-4-methylpyridine
7-chloro-1H-pyrazolo<3,4-c>pyridine
Conditions | Yield |
---|---|
With potassium acetate; sodium nitrite In water; ethyl acetate | 46% |
Multi-step reaction with 2 steps 1: 2.1 g / toluene / 2 h / 100 °C 2: 1.) phosphorus pentaoxide, potassium acetate, nitrosyl chloride, 2.) sodium carbonate / 1.) acetic acid, 2.) benzene, reflux View Scheme | |
Multi-step reaction with 4 steps 1: 2.1 g / toluene / 2 h / 100 °C 2: 1.) phosphorus pentaoxide, potassium acetate, nitrosyl chloride, 2.) sodium carbonate / 1.) acetic acid, 2.) benzene, reflux 3: 67 percent / phosphorus pentasulphide / pyridine / 4.5 h / Heating 4: 71 percent / chlorine, conc. hydrochloric acid / 0.33 h View Scheme |
6-chloropicolinic acid
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 70℃; for 15h; | 46% |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane at 50℃; for 12h; | 40% |
3-Amino-2-chloro-4-methylpyridine
(1-methyl-1H-pyrazol-5-yl)boronic acid
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 100℃; for 3h; | 30% |
3-Amino-2-chloro-4-methylpyridine
aniline
4-methyl-N2-phenylpyridine-2,3-diamine
Conditions | Yield |
---|---|
at 180℃; for 1.25h; Microwave irradiation; | 28% |
2-(2,5-dichloro-phenoxy)-nicotinic acid
3-Amino-2-chloro-4-methylpyridine
methyl iodide
N-(2-chloro-4-methylpyridin-3-yl)-2-(2,5-dichlorophenoxy)-N-methylnicotinamide
Conditions | Yield |
---|---|
Stage #1: 2-(2,5-dichloro-phenoxy)-nicotinic acid; 3-Amino-2-chloro-4-methylpyridine With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: methyl iodide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 40℃; for 2h; | 3% |
acetic anhydride
3-Amino-2-chloro-4-methylpyridine
3-acetamido-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
In toluene at 100℃; for 2h; | 2.1 g |
In dichloromethane at 20℃; | |
In dichloromethane at 20℃; for 24h; |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 73.5 percent / sodium hydride / dimethylformamide; toluene / 1 h / 40 - 45 °C 2: 63.8 percent / ethanol / 4 h / 78 - 80 °C View Scheme |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 73.5 percent / sodium hydride / dimethylformamide; toluene / 1 h / 40 - 45 °C 2: 54.7 percent / ethanol / 4 h / 78 - 80 °C View Scheme |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 73.5 percent / sodium hydride / dimethylformamide; toluene / 1 h / 40 - 45 °C 2: 74.5 percent / ethanol / 4 h / 78 - 80 °C View Scheme |
3-Amino-2-chloro-4-methylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 73.5 percent / sodium hydride / dimethylformamide; toluene / 1 h / 40 - 45 °C 2: 55.7 percent / ethanol / 4 h / 78 - 80 °C View Scheme |
Molecular structure of 3-Amino-2-chloro-4-methyl pyridine (CAS NO.133627-45-9) is:
IUPAC: 2-Chloro-4-methylpyridin-3-amine
CAS Registry Number: 133627-45-9
Molecular Formula: C6H7ClN2
Molecular Weight: 142.59
Melting Point: 61-64°C
Surface Tension: 49.9 dyne/cm
Density: 1.26 g/cm3
Flash Point: 125.2 °C
Enthalpy of Vaporization: 52.23 kJ/mol
Boiling Point: 283.3 °C at 760 mmHg
Vapour Pressure: 0.00318 mmHg at 25°C
Product Categories: Pyridine;Amines and Anilines;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Amines;Pyridines;Heterocyclic Compounds;(intermediate of nevirapine);Aromatics Compounds;Chloropyridines;Halopyridines;Aromatics;Bases & Related Reagents;Nucleotides
3-Amino-2-chloro-4-methyl pyridine (CAS NO.133627-45-9) is the important intermediates .
Safty information about 3-Amino-2-chloro-4-methyl pyridine (CAS NO.133627-45-9) is:
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S36:Wear suitable protective clothing.
RIDADR: UN2811
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
3-Amino-2-chloro-4-methyl pyridine , its cas register number is 133627-45-9. It also can be called 2-Chloro-3-amino-4-picoline .It is a off white crystals.
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