tert-butyl (4-chloropyridin-2-yl) carbamate
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h; | 100% |
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h; | 99% |
With trifluoroacetic acid In dichloromethane at 20℃; | 90% |
With hydrogen bromide for 2h; | 87% |
With hydrogen bromide for 2h; Ambient temperature; |
2,2-dimethyl-3-(4-chloropyrid-2-yl)-4-oxo-4H-1,3-benzoxazine
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With hydrogenchloride for 8h; Heating; | 95% |
With hydrogenchloride Hydrolysis; |
4-chloropicolinamide
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With bromine; potassium hydroxide In water at 90℃; for 2h; Cooling with ice; | 84% |
With calcium hypochlorite In water at 60 - 80℃; Temperature; | 81% |
With sodium hydroxide; bromine In water at 80℃; for 1.5h; Hofmann Degradation; | 64% |
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With hydrazine hydrate; sodium nitrite In hydrogenchloride; methanol; water; acetic acid | 44% |
With hydrazine hydrate; acetic acid; sodium nitrite In hydrogenchloride; methanol; water | 37 g (60%) |
2,4-dichloropyridine
A
2-Amino-4-chloropyridine
B
4-Amino-2-chloropyridine
Conditions | Yield |
---|---|
With ammonium hydroxide at 170 - 180℃; | |
With ammonium hydroxide at 180℃; |
4-chloro-pyridine-2-carbonyl azide
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With acetic acid |
A
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With hydrogenchloride at 60℃; for 3h; | A 70 mg B 45 mg |
4-chloro-2-pyridinylisocyanate
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With hydrogenchloride for 48h; Heating; Yield given; |
4-chloropyridine-2-carbohydrazide
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid; sodium nitrite 1.) water, 15 min, 2.) water, heating; Yield given. Multistep reaction; |
2,4-dichloropyridine
A
2-Amino-4-chloropyridine
B
4-Amino-2-chloropyridine
Conditions | Yield |
---|---|
at 180℃; |
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane; chloroform at 70℃; |
4-chloropyridine N-oxide
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Ts2O / CHCl3; CH2Cl2 / 0.25 h 2: TFA / CHCl3; CH2Cl2 / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: CH2Cl2 / Heating 2: conc. HCl View Scheme | |
Multi-step reaction with 2 steps 1: 90 percent / CHCl3 / 4 h / Heating 2: 95 percent / conc. HCl / 8 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 20 percent / 1,2-dichloro-ethane / 12 h / Heating 2: 90 percent / CHCl3 / 4 h / Heating 3: 95 percent / conc. HCl / 8 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 8 percent / 1,2-dichloro-ethane / 12 h / Heating 2: 95 percent / conc. HCl / 8 h / Heating View Scheme |
4-chloropicolinic acid
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenylphosphoryl azide, triethylamine / 26 h / Heating 2: 25percent HBr / 2 h / Ambient temperature View Scheme |
4-nitraminopyridine N-oxide
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuryl chloride / 110 °C 2: aqueous NH3 / 180 °C View Scheme |
3-deazauracil
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphoryl chloride / 140 °C 2: aqueous NH3 / 180 °C View Scheme |
2-picolinic acid hydrochloride
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With thionyl chloride; acetic acid; hydrazine; sodium nitrite In methanol; water |
5-bromo-4-chloro-pyridin-2-ylamine
bis(pinacol)diborane
A
2-Amino-4-chloropyridine
B
4-chloro-5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))-2-pyridylamine
Conditions | Yield |
---|---|
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 115℃; for 6.25h; Heating / reflux; | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; for 6h; Inert atmosphere; | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 115℃; for 6h; Inert atmosphere; |
2-Picolinic acid
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium bromide; thionyl chloride / chlorobenzene / 20.5 h / 50 - 85 °C 2.1: toluene / 1.5 h / 0 - 15 °C 3.1: ammonium hydroxide / 3 h / 20 °C 4.1: bromine; sodium hydroxide / water / 5 h / 20 - 80 °C 4.2: pH 12 - 13 View Scheme | |
Multi-step reaction with 4 steps 1.1: thionyl chloride / 72 h / Reflux 2.1: toluene / 1 h / 0 - 5 °C 3.1: water / 0.25 h 3.2: 1 h / 20 °C 4.1: sodium hydroxide; bromine / water / 0.58 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium bromide / thionyl chloride / Reflux 1.2: 20 °C 2.1: calcium hypochlorite / water / 60 - 80 °C View Scheme | |
Multi-step reaction with 4 steps 1: thionyl chloride / Heating / reflux 2: lithium hydroxide; water / tetrahydrofuran / 20 °C 3: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 65 - 100 °C 4: trifluoroacetic acid / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium bromide; thionyl chloride / 16 h / Reflux 2: ammonium hydroxide / 18 h / 0 - 20 °C 3: bromine; sodium hydroxide / water / 3.5 h / -10 - 100 °C View Scheme |
4-Chloro-pyridine-2-carboxylic acid methyl ester
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: ammonium hydroxide / 3 h / 20 °C 2.1: bromine; sodium hydroxide / water / 5 h / 20 - 80 °C 2.2: pH 12 - 13 View Scheme | |
Multi-step reaction with 2 steps 1.1: water / 0.25 h 1.2: 1 h / 20 °C 2.1: sodium hydroxide; bromine / water / 0.58 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 3 steps 1: lithium hydroxide; water / tetrahydrofuran / 20 °C 2: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 65 - 100 °C 3: trifluoroacetic acid / dichloromethane / 20 °C View Scheme |
4-chloropicolinic acid
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene / 1.5 h / 0 - 15 °C 2.1: ammonium hydroxide / 3 h / 20 °C 3.1: bromine; sodium hydroxide / water / 5 h / 20 - 80 °C 3.2: pH 12 - 13 View Scheme | |
Multi-step reaction with 2 steps 1.1: thionyl chloride / toluene / 6 h / 80 °C 1.2: 1 h / 20 °C / Cooling with ice 2.1: potassium hydroxide; bromine / water / 2 h / 90 °C / Cooling with ice View Scheme |
4-chloro-pyridine-2-carbonyl chloride
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene / 1 h / 0 - 5 °C 2.1: water / 0.25 h 2.2: 1 h / 20 °C 3.1: sodium hydroxide; bromine / water / 0.58 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 2 steps 1: ammonium hydroxide / 18 h / 0 - 20 °C 2: bromine; sodium hydroxide / water / 3.5 h / -10 - 100 °C View Scheme |
2-Amino-4-chloropyridine
(2-aminopyridin-4-yl)boronic acid
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; | 100% |
With potassium acetate; bis(pinacol)diborane; bis(dibenzylideneacetone)-palladium(0); XPhos In 1,4-dioxane at 110℃; |
2-Amino-4-chloropyridine
2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water; acetonitrile at 120℃; | 100% |
With tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water; acetonitrile at 90℃; for 12h; |
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
In tetrahydrofuran Reflux; | 99.9% |
Conditions | Yield |
---|---|
With triethylamine at 20 - 60℃; for 12h; | 99% |
With triethylamine at 60℃; for 12h; | 99% |
With pyridine In dichloromethane at 20℃; for 26h; | 75% |
2-Amino-4-chloropyridine
N-nitro-2-amino-4-chloropyridine
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0 - 5℃; for 78h; | 99% |
With sulfuric acid; nitric acid at 0 - 20℃; for 0.333333h; | 92% |
With sulfuric acid; nitric acid at 0℃; for 0.333333h; |
2-Amino-4-chloropyridine
pivaloyl chloride
4-chloro-2-trimethylacetamidopyridine
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12h; | 99% |
With pyridine at 0 - 20℃; for 12h; | 99% |
With pyridine for 12h; Ambient temperature; | 95% |
2-Amino-4-chloropyridine
phenyl chloroformate
phenyl N-(4-chloro-2-pyridyl)-N-phenoxycarbonylcarbamate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 25℃; for 2h; | 99% |
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; | 53.4% |
2-Amino-4-chloropyridine
dimethyl amine
2-amino-4-(dimethylamino)-pyridine
Conditions | Yield |
---|---|
In water at 120℃; Microwave irradiation; | 99% |
In water at 175℃; for 0.583333h; Microwave; | 94% |
Stage #1: 2-Amino-4-chloropyridine; dimethyl amine In water at 175℃; for 0.583333h; Microwave irradiation; Stage #2: With ammonium carbonate In water; acetonitrile | 94% |
In water at 175℃; for 0.583333h; Microwave irradiation; | 94% |
2-Amino-4-chloropyridine
5-bromo-4-chloro-pyridin-2-ylamine
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile for 14h; | 99% |
With N-Bromosuccinimide In acetonitrile at 20℃; for 14h; | 99% |
With N-Bromosuccinimide In acetonitrile at 20℃; | 99% |
2-Amino-4-chloropyridine
cyclopropylboronic acid
2-amino-4-(cyclopropyl)pyridine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tricyclohexylphosphine In 1,4-dioxane; acetonitrile at 120℃; Inert atmosphere; | 99% |
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 15h; |
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction; | 99% |
2-Amino-4-chloropyridine
tert-butyl (azetidin-3-ylmethyl)carbamate hydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube; | 96% |
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube; |
2-Amino-4-chloropyridine
Methoxyacetyl chloride
N-(4-chloro-2-pyridyl)-2-methoxyacetamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20 - 25℃; for 0.25h; | 96% |
2-Amino-4-chloropyridine
ibuprofen
Conditions | Yield |
---|---|
Stage #1: ibuprofen With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 2-Amino-4-chloropyridine In dichloromethane for 72h; Heating; | 95% |
2-Amino-4-chloropyridine
ethyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)propenoate
Conditions | Yield |
---|---|
With acetic acid for 4h; Heating; | 95% |
2-Amino-4-chloropyridine
3-pyridylboronic acid
4-(pyridin-3-yl)pyridin-2-amine
Conditions | Yield |
---|---|
With potassium phosphate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In 1,4-dioxane; water at 100℃; Suzuki-Miyaura cross-coupling; | 95% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In acetonitrile at 170℃; Suzuki reaction; Microwave irradiation; | 95% |
2-Amino-4-chloropyridine
Ethoxycarbonyl isothiocyanate
ethyl [(4-chloropyridin-2-yl)carbamothioyl]carbamate
Conditions | Yield |
---|---|
In 1,4-dioxane at 20℃; | 95% |
In 1,4-dioxane at 25℃; for 2h; | 92.1% |
In 1,4-dioxane at 20℃; for 2h; | 16.5 g |
In 1,4-dioxane at 20℃; for 2h; | 8.5 g |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(l) iodide In water at 20℃; for 6h; | 95% |
2-Amino-4-chloropyridine
3-chlorobenzoate
3-chloro-N-(4-chloropyridin-2-yl)benzamide
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 94% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane |
2-Amino-4-chloropyridine
2-(2-methoxyethoxy)ethyl alcohol
Conditions | Yield |
---|---|
Stage #1: 2-(2-methoxyethoxy)ethyl alcohol With sodium hydride In neat (no solvent) for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: 2-Amino-4-chloropyridine In neat (no solvent) at 120℃; for 16h; Sealed tube; | 94% |
Conditions | Yield |
---|---|
Stage #1: 2-Amino-4-chloropyridine With n-butyllithium In hexane at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: (N,N-dimethylamino)dimethylchlorosilane In hexane at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique; | 94% |
2-Amino-4-chloropyridine
tert-butylisonitrile
Glyoxilic acid
C11H14ClN3
Conditions | Yield |
---|---|
Stage #1: 2-Amino-4-chloropyridine; Glyoxilic acid With perchloric acid In methanol Groebke-Blackburn-Bienayme reaction; Stage #2: tert-butylisonitrile In methanol at 20℃; for 12h; Groebke-Blackburn-Bienayme reaction; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(l) iodide In water at 20℃; for 6h; | 93% |
2-Amino-4-chloropyridine
2-bromo-4-chloropyridine
Conditions | Yield |
---|---|
Stage #1: 2-Amino-4-chloropyridine With hydrogen bromide; bromine In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at -10 - 20℃; Stage #3: With sodium hydroxide In water at 0℃; pH=> 10; | 92% |
Stage #1: 2-Amino-4-chloropyridine With hydrogen bromide; bromine In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at -10 - 20℃; Stage #3: With sodium hydroxide In water at 0℃; pH=10; | 92% |
Stage #1: 2-Amino-4-chloropyridine With hydrogen bromide; bromine In water at -5℃; for 0.333333h; Stage #2: With sodium nitrite In water at -5℃; for 0.5h; | 40% |
2-Amino-4-chloropyridine
tert-butyl N-(4-piperidinylmethyl)carbamate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube; | 92% |
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube; |
2-Amino-4-chloropyridine
ortho-bromobenzaldehyde
Conditions | Yield |
---|---|
With choline azide; caesium carbonate at 20℃; for 4h; Green chemistry; | 92% |
4,4-dimethylpiperidine
2-Amino-4-chloropyridine
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 200℃; for 0.75h; Microwave irradiation; | 92% |
2-Amino-4-chloropyridine
4-chloro-5-iodopyridin-2-ylamine
Conditions | Yield |
---|---|
With N-iodo-succinimide In N,N-dimethyl-formamide for 43h; regioselective reaction; | 90% |
With N-iodo-succinimide In N,N-dimethyl-formamide at 40℃; | 70% |
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 18h; | 62% |
The 4-Chloro-pyridin-2-ylamine is an organic compound with the formula C5H5ClN2. The IUPAC name of this chemical is 4-chloropyridin-2-amine. With the CAS registry number 19798-80-2, it is also named as 2-Pyridinamine, 4-chloro-. The product's categories are Pyridine; Blocks; Pyridines; Amines and Anilines; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; Heterocyclic Series; Pharmacetical; Pyridine Series; Amines; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides; Pharmaceutical Intermediate; Amino-Pyridine Eeries.
Physical properties about 4-Chloro-pyridin-2-ylamine are: (1)ACD/LogP: 1.32; (2)ACD/LogD (pH 5.5): 0.897; (3)ACD/LogD (pH 7.4): 1.308; (4)ACD/BCF (pH 5.5): 2.244; (5)ACD/BCF (pH 7.4): 5.785; (6)ACD/KOC (pH 5.5): 47.149; (7)ACD/KOC (pH 7.4): 121.544; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)Polar Surface Area: 38.91 Å2; (11)Index of Refraction: 1.607; (12)Molar Refractivity: 33.475 cm3; (13)Molar Volume: 96.888 cm3; (14)Polarizability: 13.271×10-24cm3; (15)Surface Tension: 54.396 dyne/cm; (16)Density: 1.327 g/cm3; (17)Flash Point: 99.428 °C; (18)Enthalpy of Vaporization: 47.772 kJ/mol; (19)Boiling Point: 240.793 °C at 760 mmHg; (20)Vapour Pressure: 0.037 mmHg at 25°C.
Preparation: this chemical can be prepared by t-butyl N-(4-chloro-2-pyridinyl)carbamate. This reaction will need reagent 25 percent HBr. The reaction time is 2 hours. The yield is about 87%.
Uses of 4-Chloro-pyridin-2-ylamine: it can be used to produce 4-methoxy-pyridin-2-ylamine at temperature of 140 °C. It will need solvent methanol with reaction time of 7 hours. The yield is about 44%.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin.
You can still convert the following datas into molecular structure:
(1)SMILES: c1cnc(cc1Cl)N
(2)InChI: InChI=1/C5H5ClN2/c6-4-1-2-8-5(7)3-4/h1-3H,(H2,7,8)
(3)InChIKey: RQMWVVBHJMUJNZ-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C5H5ClN2/c6-4-1-2-8-5(7)3-4/h1-3H,(H2,7,8)
(5)Std. InChIKey: RQMWVVBHJMUJNZ-UHFFFAOYSA-N
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