6298-19-7

Basic information

• Product Name: 2-Chloro-3-pyridinamine
• Synonyms: 3-AMINOCHLOROPYRIDINE;3-AMINO-2-CHLOROPYRIDINE;AKOS MSC-0729;2-CHLORO-3-AMINOPYRIDINE;2-CHLORO-3-PYRIDYLAMINE;2-Chloro-3-pyridinamine;2-CHLORO-B-PYRIDYLAMINE;2-CHLORO-PYRIDIN-3-YLAMINE
• CAS NO: 6298-19-7
• Molecular Formula: C₅H₅ClN₂
• Molecular Weight: 128.56
• EINECS: 228-572-9
• Product Categories: PYRIDINE;Amines;blocks;Pyridines;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Pyridine series;Chloropyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pharmaceutical intermediate;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;amine | alkyl chloride
• Mol File: 6298-19-7.mol
• Article Data: 66

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 130-134 °C (12.7517 mmHg)
• Flash Point: 185 °C
• Appearance: Off-white to yellow to pink/Crystalline Powder, Crystals, and/or Chunks
• Density: 130
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 30g/l
• PKA: 2.42±0.10(Predicted)
• Water Solubility: Soluble in methanol and water. (30 g/L).
• BRN: 109814
• CAS DataBase Reference: 2-Chloro-3-pyridinamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-pyridinamine(6298-19-7)
• EPA Substance Registry System: 2-Chloro-3-pyridinamine(6298-19-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6298-19-7(Hazardous Substances Data)

Usage

Description

2-Chloro-3-pyridinamine is an organic compound with the chemical formula C5H5ClN2. It is an off-white to yellow to pink crystalline powder and is known for its role as an intermediate in the synthesis of various pharmaceuticals and agricultural chemicals. This versatile compound is also involved in Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds, which are significant in the formation of complex molecular structures.

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-pyridinamine is used as a chemical intermediate for the synthesis of various medications. Its presence in the development process is crucial due to its ability to form complex molecular structures, which can be tailored for specific therapeutic applications.
Used in Agricultural Chemicals Industry:
In the agricultural chemicals industry, 2-Chloro-3-pyridinamine is utilized as an intermediate in the production of pesticides and other agrochemicals. Its involvement in the synthesis process contributes to the development of effective compounds that can protect crops from pests and diseases.
Used in Chemical Synthesis:
2-Chloro-3-pyridinamine is used as a key component in Suzuki-Miyaura cross-coupling reactions, which are essential for the formation of heteroaryl compounds. These reactions play a significant role in the creation of complex molecular structures with potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.
Overall, 2-Chloro-3-pyridinamine is a versatile compound with applications in multiple industries, primarily due to its role as a chemical intermediate and its involvement in crucial chemical reactions.

InChI:InChI=1/C5H5ClN2/c6-5-4(7)2-1-3-8-5/h1-3H,7H2

Synthetic route

2-Chloro-3-nitropyridine (5470-18-8) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
Stage #1: 2-Chloro-3-nitropyridine In water at 20℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In water Inert atmosphere;	99%
With sodium tetrahydroborate In water at 20℃; for 24h;	99%
With titanium for 0.25h; Ambient temperature;	98%

pyridin-3-ylamine (462-08-8) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite In chloroform at 10 - 30℃; Solvent; Temperature; Reagent/catalyst;	93.1%
With hydrogenchloride; dihydrogen peroxide	82%
Stage #1: pyridin-3-ylamine With hydrogenchloride; iron(III) chloride; chlorine In water Stage #2: With sodium hydroxide In water pH=9 - 11;	75%

3-azido-2-chloropyridine (102934-51-0) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With iron In water at 20℃; Inert atmosphere;	87%
With 2,6-di-tert-butyl-4-methyl-phenol In decalin at 144.3℃; Kinetics; Rate constant; Thermodynamic data; var. conc. of inhibitor;

nicotinamide (98-92-0) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With sodium hydroxide; chlorine r.t., 30 min.; then 65-75 deg C, 2 h;	78.6%
With sodium hypochlorite
With sodium hydroxide; chlorine Heating;
Multi-step reaction with 2 steps 1: sodium hypochlorite / water / 2.5 h / 0 - 100 °C 2: dihydrogen peroxide / 1 h / 5 - 15 °C View Scheme

pyridin-3-ylamine (462-08-8) → 2-chloro-3-aminopyridine (6298-19-7) + 3-amino-2,6-dichloropyridine (62476-56-6)

Conditions	Yield
Stage #1: pyridin-3-ylamine With hydrogenchloride In water at 30 - 35℃; Stage #2: With dihydrogen peroxide In water at 10 - 19℃; for 8.33333h; Stage #3: With sodium hydroxide In water; toluene at 25 - 35℃; Product distribution / selectivity;	A 76% B n/a
Stage #1: pyridin-3-ylamine With hydrogenchloride In water at 30 - 35℃; Stage #2: With chlorine In water at 15 - 20℃; for 1.5h; Stage #3: With sodium hydroxide In toku; water at 25 - 40℃; Product distribution / selectivity;	A 74% B n/a
With hydrogenchloride

2-chloronicotinamide (10366-35-5) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With sodium hydroxide; bromine In water 1.) 5 deg C; 2.) 75 deg C;	72%
With sodium hydroxide; bromine In methanol; water	72%
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement;

2-Chloro-3-nitropyridine (5470-18-8) + acrylic acid methyl ester (292638-85-8) → 2-chloro-3-aminopyridine (6298-19-7) + methyl 3-[(2-chloro-3-pyridyl)amino]propanoate (1093347-31-9)

Conditions	Yield
With phenyl(2-pyridinyl)methanol In acetonitrile at 110℃; for 96h; Inert atmosphere;	A 8% B 68%

methyllithium (917-54-4) + 2-(2-Chloro-pyridin-3-ylamino)-2-methyl-propionitrile → 2-chloro-3-aminopyridine (6298-19-7) + 2-Chloro-3-<(1,1-dimethylethyl)amino>pyridine (151414-96-9)

Conditions	Yield
In diethyl ether; toluene 1.) -78 deg C, 30 min, 2.) r.t., 8 h;	A 15% B 64%
In diethyl ether; toluene Mechanism; Product distribution; 1.) -78 deg C, 30 min, 2.) r.t., 8 h, - other organometallic reagents, other solvents;	A 15% B 64%

C25H43ClN2O5S2Si (1609941-98-1) → 2-chloro-3-aminopyridine (6298-19-7) + C21H37ClN2O4SSi (1609942-00-8)

Conditions	Yield
Stage #1: C25H43ClN2O5S2Si In diphenylether at 200℃; Brook Silaketone Rearrangement; Inert atmosphere; Stage #2: With di-tert-butyl peroxide In chlorobenzene Brook Silaketone Rearrangement; Inert atmosphere; Reflux;	A 41% B 55%

2-Chloro-3-nitropyridine (5470-18-8) + boron dimethyl-trifluoro sulphide (353-43-5) → 2-chloro-3-aminopyridine (6298-19-7) + 2-chloro-6-(methylthio)pyridin-3-amine

Conditions	Yield
In dichloromethane at 60℃; for 4h; Sealed tube;	A 51% B 21%

2-Chloro-3-nitropyridine (5470-18-8) → 2-chloro-3-aminopyridine (6298-19-7) + N-(2-chloropyridin-3-yl)hydroxylamine (67119-49-7)

Conditions	Yield
With ammonium chloride; zinc In ethanol; water at 70℃; for 0.333333h; various conditions;	A 25% B 45%
With baker's yeast; D-glucose In phosphate buffer; ethanol at 30℃; for 3h; pH=6.5;
With cyclohexa-1,4-diene; 5% platinum on carbon In methanol at 100℃; for 0.166667h; Microwave irradiation;

2-chloro-3-hydroxypyridine (6636-78-8) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With potassium carbonate; potassium iodide; Chloroacetamide In N,N-dimethyl-formamide at 90 - 150℃; for 4h; Smiles Aromatic Rearrangement;	42%

2-Chloro-3-nitropyridine (5470-18-8) → 2-chloro-3-aminopyridine (6298-19-7) + 3-nitropyridine (2530-26-9)

Conditions	Yield
With Me2SiI In chloroform at 20℃; for 2h;	A 29% B 41%

C25H43ClN2O5S2Si (1609941-98-1) → 2-chloro-3-aminopyridine (6298-19-7) + C21H37ClN2O4SSi (1609941-99-2) + C16H32O4SSi (1609942-01-9)

Conditions	Yield
In diphenylether at 200℃; Inert atmosphere;	A n/a B n/a C 39%

2-Chloro-3-nitropyridine (5470-18-8) + carbon monoxide (201230-82-2) + butan-1-ol (71-36-3) → 2-chloro-3-aminopyridine (6298-19-7) + n-Butyl 3-aminopyridine-2-carboxylate + 3-nitro-pyridine-2-carboxylic acid butyl ester

Conditions	Yield
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride at 130℃; under 18751.5 Torr; for 15h;	A n/a B 35% C 25%

3-amino-2-ethoxypyridine (51468-01-0) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate at 130℃; for 24h;	31%

3-amino-2-methoxypyridine (20265-38-7) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate at 130℃; for 24h;	30%

2-(benzyloxy)pyridin-3-amine (23845-96-7) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate at 130℃; for 24h;	28%

3-amino-2-bromopyridine (39856-58-1) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With hydrogenchloride

pyridin-3-ylamine (462-08-8) + hydrogenchloride (7647-01-0) + water (7732-18-5) + dihydrogen peroxide (7722-84-1) → 2-chloro-3-aminopyridine (6298-19-7) + 3-amino-2,6-dichloropyridine (62476-56-6)

Conditions	Yield
at 80℃;

pyridin-3-ylamine (462-08-8) + hydrogenchloride (7647-01-0) + water (7732-18-5) + dihydrogen peroxide (7722-84-1) → 2-chloro-3-aminopyridine (6298-19-7) + 3-amino-2,6-dichloropyridine (62476-56-6) + 2,4,5,6-tetrachloro-[3]pyridylamine

Conditions	Yield
at 110℃;

2-hydroxy-3-nitropyridine (6332-56-5) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride; phosphorus (V)-chloride 2: iron; acetic acid View Scheme
Multi-step reaction with 3 steps 1: bromine; phosphorus (III)-bromide / 100 °C 2: iron-turnings; acetic acid / 100 °C 3: concentrated aqueous HCl View Scheme

2-bromo-3-nitropyridine (19755-53-4) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: iron-turnings; acetic acid / 100 °C 2: concentrated aqueous HCl View Scheme

N-monochloronicotinamide (63458-55-9) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
Stage #1: N-monochloronicotinamide In water at 75 - 81℃; for 0.916667h; Stage #2: With hydrogenchloride In water at 15 - 50℃; Stage #3: With sodium hydroxide; dihydrogen peroxide; sodium hydrogensulfite Product distribution / selectivity; more than 3 stages;

2-Chloro-3-nitropyridine (5470-18-8) + phenyl(2-pyridinyl)methanol (31796-72-2) → 2-chloro-3-aminopyridine (6298-19-7) + phenyl(pyridin-2-yl)methanone (91-02-1)

Conditions	Yield
In toluene at 110℃; for 96h;

2-Chloro-3-nitropyridine (5470-18-8) → pyridin-3-ylamine (462-08-8) + 2-chloro-3-aminopyridine (6298-19-7) + N-(2-chloropyridin-3-yl)hydroxylamine (67119-49-7)

Conditions	Yield
With cyclohexa-1,4-diene; 5% platinum on carbon In methanol at 120℃; for 0.133333h; Microwave irradiation;

3-[(t-butoxycarbonyl)amino]-2-methoxyisonicotinic acid (870997-82-3) → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With trifluoroacetic acid In dichloromethane

2-Chloro-3-nitropyridine (5470-18-8) → pyridin-3-ylamine (462-08-8) + 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 80℃; for 0.0833333h; Overall yield = 85 %;

C11H21ClN2Si2 → 2-chloro-3-aminopyridine (6298-19-7)

Conditions	Yield
With hydrogenchloride In chloroform; water for 1h;	46.8 mg

2-chloro-3-aminopyridine (6298-19-7) + pivaloyl chloride (3282-30-2) → N-2-chloropyrid-3-yl-trimethylacetamide (109902-33-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; Acylation;	100%
With triethylamine In tetrahydrofuran; diethyl ether	90%
With triethylamine In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; Schlenk technique;	83%

2-chloro-3-aminopyridine (6298-19-7) + 2-nitrobenzyl chloride (610-14-0) → N-(2-chloro-pyridin-3-yl)-2-nitro-benzamide (1028-86-0)

Conditions	Yield
With pyridine at 0 - 20℃;	100%
With pyridine In tetrahydrofuran at 20℃; for 2h;	100%
In pyridine 1. -10 deg C 2. 15h, r. t.;	96%

2-chloro-3-aminopyridine (6298-19-7) + 2-Methoxypropene (116-11-0) → (2-Chloropyridin-3-yl)(1-methylethylidene)amine (51468-05-4)

Conditions	Yield
With pyridinium p-toluenesulfonate; triethylamine In chloroform at 100℃; for 9h;	100%

2-chloro-3-aminopyridine (6298-19-7) + N-ethoxycarbonyl-4-piperidone (29976-53-2) → 4-(2-chloropyridin-3-ylamino)piperidine-1-carboxylic acid ethyl ester (906371-78-6)

Conditions	Yield
Stage #1: 2-chloro-3-aminopyridine; N-ethoxycarbonyl-4-piperidone With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 16 - 56℃; for 0.333333h; Stage #2: With sodium hydroxide In Isopropyl acetate; water at 80℃; for 0.166667h; pH=8 - 9; Product distribution / selectivity;	100%
Stage #1: 2-chloro-3-aminopyridine; N-ethoxycarbonyl-4-piperidone In Isopropyl acetate at 16℃; for 0.0833333h; Stage #2: With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 16 - 56℃; for 0.258333h; Stage #3: With sodium hydroxide In Isopropyl acetate; water at 50℃; for 0.166667h; pH=8 - 9;	100%
Stage #1: 2-chloro-3-aminopyridine; N-ethoxycarbonyl-4-piperidone In Isopropyl acetate for 0.25h; Industry scale; Stage #2: With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 20 - 27℃; for 3h; Industry scale; Stage #3: With sodium hydroxide In Isopropyl acetate; water at 20 - 60℃; pH=11; Product distribution / selectivity; Industry scale;	100%

2-chloro-3-aminopyridine (6298-19-7) + acetyl chloride (75-36-5) → N-(2-chloro-3-pyridinyl)acetamide (21352-19-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In tetrahydrofuran at 70℃; for 8h;	84%
With triethylamine In dichloromethane	62%
With triethylamine In dichloromethane at 0 - 20℃;	62%

2-chloro-3-aminopyridine (6298-19-7) + benzyl 4-oxo-1-piperidinecarboxylate (19099-93-5) → benzyl 4-(2-chloro-pyridin-3-yl-amino)-piperidine-1-carboxylate (1146637-14-0)

Conditions	Yield
Stage #1: 2-chloro-3-aminopyridine; benzyl 4-oxo-1-piperidinecarboxylate With sodium tris(acetoxy)borohydride; trifluoroacetic acid In isopropyl alcohol at 15℃; Stage #2: With sodium hydroxide In isopropyl alcohol at 20℃;	100%
Stage #1: 2-chloro-3-aminopyridine; benzyl 4-oxo-1-piperidinecarboxylate With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 15℃; Stage #2: With sodium hydroxide In Isopropyl acetate; water at 20℃;	100%
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 15℃;
Stage #1: 2-chloro-3-aminopyridine; benzyl 4-oxo-1-piperidinecarboxylate With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 15℃; Stage #2: With sodium hydroxide In Isopropyl acetate; water

2-chloro-3-aminopyridine (6298-19-7) + acetone (67-64-1) → (2-chloro-pyridin-3-yl)-isopropyl-amine (160843-96-9)

Conditions	Yield
Stage #1: 2-chloro-3-aminopyridine; acetone With dimethylsulfide borane complex; acetic acid In dichloromethane at 0 - 20℃; Stage #2: With ammonia In dichloromethane; water pH=8;	100%
With dimethylsulfide borane complex; acetic acid In dichloromethane at 0 - 20℃;	99%
With borane dimethyl sulfide complex In dichloromethane; acetic acid at 0 - 20℃;
Stage #1: 2-chloro-3-aminopyridine; acetone With acetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane for 24h;	1.2 g

2-chloro-3-aminopyridine (6298-19-7) + dimedone (126-81-8) → C13H15ClN2O (1217862-29-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 24h; Reflux;	100%

2-chloro-3-aminopyridine (6298-19-7) + 4-nitro-benzoyl chloride (122-04-3) → N-(2-Chloro-pyridin-3-yl)-4-nitro-benzamide (121311-55-5)

Conditions	Yield
In pyridine at 12 - 14℃;	99%
With pyridine

2-chloro-3-aminopyridine (6298-19-7) + m-nitrobenzoic acid chloride (121-90-4) → N-(2-Chloro-pyridin-3-yl)-3-nitro-benzamide (121311-54-4)

Conditions	Yield
In pyridine at 12 - 14℃;	99%
With pyridine

2-chloro-3-aminopyridine (6298-19-7) + 1,3-cylohexanedione (504-02-9) → 3-[(2-chloro-3-pyridinyl)amino]cyclohex-2-en-1-one (198141-10-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Condensation; Heating;	99%

2-chloro-3-aminopyridine (6298-19-7) + trifluoroacetic anhydride (407-25-0) → N-(2-chloropyridin-3-yl)-2,2,2-trifluoroacetamide (574714-02-6)

Conditions	Yield
In dichloromethane for 1.33333h;	99%
With triethylamine In dichloromethane at 0 - 25℃; for 12h; Inert atmosphere;	93%
In dichloromethane for 2.33333h;

2-chloro-3-aminopyridine (6298-19-7) + 4-chlorobenzaldehyde (104-88-1) → 2-chloro-N-(4-chlorobenzyl)pyridin-3-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In ethyl acetate for 0.166667h;	99%

2-chloro-3-aminopyridine (6298-19-7) + 2-furancarbonyl chloride (527-69-5) → N-(2-chloro-3-pyridinyl)-2-furylamide (91813-34-2)

Conditions	Yield
In pyridine at -10℃; for 5h;	98%

2-chloro-3-aminopyridine (6298-19-7) + 2,5-hexanedione (110-13-4) → 1-(2-chloropyridin-3-yl)-2,5-dimethyl-1H-pyrrole

Conditions	Yield
montmorillonite K-10 at 90℃; for 0.0333333h; modified Paal-Knorr synthesis; microwave heating;	98%
With toluene-4-sulfonic acid In toluene for 2h; Heating;	93%

2-chloro-3-aminopyridine (6298-19-7) + 2-isopropoxyphenylboronic acid (138008-97-6) → 6-(2-isopropoxyphenyl)-pyridin-5-ylamine (1482498-31-6)

Conditions	Yield
With potassium phosphate monohydrate; Ethyl 4-bromobenzoate; C52H49PRu; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 1.16667h; Suzuki-Miyaura Coupling; Inert atmosphere;	98%

2-chloro-3-aminopyridine (6298-19-7) + m-tolylboronic acid (17933-03-8) → 2-(m-tolyl)pyridin-3-amine

Conditions	Yield
Stage #1: 2-chloro-3-aminopyridine; m-tolylboronic acid With benzaldehyde In toluene at 20℃; for 0.166667h; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In toluene for 0.25h; Inert atmosphere; Stage #3: With sodium carbonate In water; toluene Reflux;	98%

2-chloro-3-aminopyridine (6298-19-7) + phenylboronic acid (98-80-6) → 3-amino-2-phenylpyridine (101601-80-3)

Conditions	Yield
With Pd(II)/C; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 80℃; for 9h; Suzuki-Miyaura coupling;	97%
With sodium carbonate; benzaldehyde; triphenylphosphine; palladium diacetate In water; toluene	97%
Stage #1: 2-chloro-3-aminopyridine; phenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;	97%

2-chloro-3-aminopyridine (6298-19-7) + 2-methoxypyridin-3-yl-boronic acid (163105-90-6) → 2'-methoxy-[2,3']bipyridinyl-3-ylamine (835876-06-7)

Conditions	Yield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;	97%
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 8h; Suzuki cross-coupling; Heating;	69%

2-chloro-3-aminopyridine (6298-19-7) + 4-methoxy-benzaldehyde (123-11-5) → (2-chloropyridin-3-yl)-(4-methoxybenzyl)amine (906371-79-7)

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 20℃; for 0.166667h;	97%
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In Isopropyl acetate at 20℃; for 0.166667h;

2-chloro-3-aminopyridine (6298-19-7) + fur-2-ylboronic acid (13331-23-2) → 2-(furan-2-yl)pyridin-3-amine (886508-57-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In chloroform; water at 80 - 100℃; for 0.333333h; Suzuki Coupling;	97%
With 2-[5-(4-methylphenyl)isoxazol-3-yl]-5-(5-phenylisoxazol-3-yl)-1,3,4-oxadiazole·2PdCl2; tetrabutylammomium bromide; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki Coupling;	96%
With PdCl2-[5-(1,1'-biphenyl-4-yl)isoxazole-3-carbaldehyde oxime]; potassium carbonate In methanol; water at 100℃; for 0.0833333h; Suzuki Coupling;	95%

2-chloro-3-aminopyridine (6298-19-7) + o-chlorobenzoyl chloride (609-65-4) → 3-(2'-chlorobenzoyl)amino-2-chloropyridine (84446-21-9)

Conditions	Yield
In pyridine 1. -10 deg C 2. 15h r. t.;	96%
With pyridine In toluene for 1h; Heating;
With pyridine In dichloromethane at 0 - 20℃;

2-chloro-3-aminopyridine (6298-19-7) + 4-methyl-benzoyl chloride (874-60-2) → 3-(p-toluoylamino)-2-chloropyridine (33761-26-1)

Conditions	Yield
In pyridine 1. -10 deg C 2. 15h, r. t.;	96%

2-chloro-3-aminopyridine (6298-19-7) + 4-methoxy-benzoyl chloride (100-07-2) → 3-(4-anisoylamino)-2-chloropyridine (126921-77-5)

Conditions	Yield
In pyridine 1. -10 deg C 2. 15h, r. t.;	96%
With pyridine In dichloromethane at 0 - 20℃;

2-chloro-3-aminopyridine (6298-19-7) + 2-Fluorobenzoyl chloride (393-52-2) → 3-(2-fluorobenzoylamino)-2-chloropyridine (126921-76-4)

Conditions	Yield
In pyridine 1. -10 deg C 2. 15 h r. t.;	96%

2-chloro-3-aminopyridine (6298-19-7) + tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) → 2-Chloro-3-<(1,1-dimethylethyl)amino>pyridine (151414-96-9)

Conditions	Yield
With boron trifluoride diethyl etherate In cyclohexane at 20℃; for 8h; Inert atmosphere;	96%

2-chloro-3-aminopyridine (6298-19-7) + tert-butoxycarbonylamino-5-(4-methoxyphenyl)-1,3,4-oxadiazole → 1-(2-chloropyridin-3-yl)-3-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)urea

Conditions	Yield
With [m-(1,4-diazabicyclo[2.2.2]octanekN1:kN4)]hexamethyldialuminum In tetrahydrofuran-d8 for 0.116667h; Microwave irradiation;	96%

2-chloro-3-aminopyridine (6298-19-7) → 2,3-dichloro-pyridine (2402-77-9)

Conditions	Yield
Stage #1: 2-chloro-3-aminopyridine With hydrogenchloride; sodium nitrite In water at 5 - 15℃; for 0.75h; Stage #2: With hydrogenchloride; aminosulfonic acid; copper(II) chloride dihydrate In water at 55 - 62℃; Product distribution / selectivity;	95%
With hydrogenchloride; thionyl chloride; nitric acid In water at 0 - 5℃;	91%
With hydrogenchloride; sodium nitrite In water at -5 - 40℃; for 1h; Sandmeyer Reaction; Cooling with ice; Inert atmosphere;	83%

2-chloro-3-aminopyridine (6298-19-7) + 2-Thiophenecarbonyl chloride (5271-67-0) → N-(2-chloro-3-pyridinyl)-2-thienylamide (91813-35-3)

Conditions	Yield
In pyridine at -10℃; for 5h;	95%
With pyridine In dichloromethane at 0℃; for 3h;	400 mg

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 39856-58-1 3-amino-2-bromopyridine 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 98-92-0 nicotinamide 
• 917-54-4 methyllithium 
• 151414-95-8 2-(2-Chloro-pyridin-3-ylamino)-2-methyl-propionitrile 
• 102934-51-0 3-azido-2-chloropyridine 
• 10366-35-5 2-chloronicotinamide 
• 20265-38-7 3-amino-2-methoxypyridine 
• 51468-01-0 3-amino-2-ethoxypyridine 
• 23845-96-7 2-(benzyloxy)pyridin-3-amine 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 439571-80-9 N²-propyl-pyridine-2,3-diyldiamine 
• 21352-19-2 N-(2-chloro-3-pyridinyl)acetamide 
• 41082-18-2 N²-cyclohexylpyridine-2,3-diamine 
• 5028-25-1 3-Amino-2-dimethylaminopyridine 
• 41010-49-5 3-amino-2-phenylaminopyridine 
• 100062-14-4 N-(2-chloropyridin-3-yl)-4-methylbenzenesulfonamide 
• 5028-20-6 3-amino-2-methylaminopyridine 
• 462-08-8 pyridin-3-ylamine 
• 2402-77-9 2,3-dichloro-pyridine 
• 452-58-4 2,3-Diaminopyridine 
• 20265-38-7 3-amino-2-methoxypyridine 
• 51468-01-0 3-amino-2-ethoxypyridine 
• 6636-78-8 2-chloro-3-hydroxypyridine 
• 31784-70-0 2-aminothiazolo<5,4-b>pyridine 

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