3430-10-2

Basic information

• Product Name: 3-Amino-2-picoline
• Synonyms: 2-METHYLPYRIDIN-3-AMINE;2-METHYL-PYRIDIN-3-YLAMINE;2-METHYL-3-PYRIDINAMINE;3-AMINO-2-METHYLPYRIDINE;3-AMINO-2-PICOLINE;2-Methyl-3-Aminoyridine;2-Methyl-3-pyridinamine 3-Amino-2-picoline;3-Pyridinamine,2-methyl-(9CI)
• CAS NO: 3430-10-2
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.14
• EINECS: -0
• Product Categories: compounds of pyridine;VARIOUSAMINE;PYRIDINE;Pyridines;Pyridine Series
• Mol File: 3430-10-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 114-119°C
• Boiling Point: 236.846 °C at 760 mmHg
• Flash Point: 120.083 °C
• Appearance: White to tan/Powder or Crystalline Powder
• Density: 1.068 g/cm³
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 6.89±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-2-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-2-picoline(3430-10-2)
• EPA Substance Registry System: 3-Amino-2-picoline(3430-10-2)

Safety Data

• Hazard Codes: Xi,T,Xn,C
• Statements: 22-37/38-41-36/37/38-34
• Safety Statements: 26-36/39-45-36/37/39-36-27
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3430-10-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Cryst

InChI:InChI=1/C6H8N2/c1-5-6(7)3-2-4-8-5/h2-4H,7H2,1H3

Synthetic route

2,2-dimethyl-3-(2-methylpyrid-3-yl)-4-oxo-4H-1,3-benzoxazine (76809-24-0) → 2-methyl-3-pyridinamine (3430-10-2) + salicylic acid (69-72-7)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	A 93% B n/a

2-methyl-3-nitropyridine (18699-87-1) → 2-methyl-3-pyridinamine (3430-10-2)

Conditions	Yield
With iron; acetic acid for 2h; Heating;	90%
With hydrogen; triethylamine; palladium 10% on activated carbon In methanol at 20℃; under 760.051 Torr; for 6h;

3-aminopyridine-2-acetic acid (80352-63-2) → 2-methyl-3-pyridinamine (3430-10-2)

Conditions	Yield
In ethanol for 5h; Heating;	86%

6-chloro-4-methyl-3-nitropyridine (22280-60-0) → 2-methyl-3-pyridinamine (3430-10-2)

Conditions	Yield
With palladium on carbon; hydrogen	66%
With methanol; Lindlar's catalyst Hydrogenation;
With methanol; palladium on activated charcoal Hydrogenation;
With sulfuric acid; zinc

2-methyl-3-pyridyl tosylate (1260000-13-2) → 2-methyl-3-pyridinamine (3430-10-2)

Conditions	Yield
Stage #1: 2-methyl-3-pyridyl tosylate With [(k2-P,N-di(1-adamantyl)-2-morpholinophenylphosphine)Pd(Ph)Cl]; sodium t-butanolate In 1,4-dioxane Inert atmosphere; Glovebox; Stage #2: With ammonia In 1,4-dioxane at 24℃; Inert atmosphere; Glovebox;	46%

2-chloro-3-aminopyridine (6298-19-7) + dihydroxy-methyl-borane (13061-96-6) → 2-methyl-3-pyridinamine (3430-10-2)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 120h; Suzuki reaction; Heating;	35%

2-methyl-3-pyridinamine (3430-10-2) + 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (16019-33-3) → N-[2-(4,6-dichloro-5-pyrimidinyl)ethyl]-2-methyl-3-pyridinamine (1001398-59-9)

Conditions	Yield
Stage #1: 2-methyl-3-pyridinamine With trifluoroacetic acid at -15℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride for 0.5h; Stage #3: 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde With water; sodium hydrogencarbonate more than 3 stages;	100%
With sodium cyanoborohydride; acetic acid In methanol at -15 - 20℃; for 19h;

2-methyl-3-pyridinamine (3430-10-2) + (7aSR,11aSR)-9-oxo-11a-(2,2,2-trifluoro-ethyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid → (7aSR,11aSR)-9-oxo-11a-(2,2,2-trifluoro-ethyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

Conditions	Yield
Stage #1: (7aSR,11aSR)-9-oxo-11a-(2,2,2-trifluoro-ethyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate In tetrahydrofuran for 0.333333h; Stage #2: 2-methyl-3-pyridinamine In tetrahydrofuran at 20 - 60℃; for 77h;	100%

2-methyl-3-pyridinamine (3430-10-2) + (7aSR,11aRS)-methyl 11a-ethyl-7,7a,8,10,11,11a-hexahydro-6H-spiro[dibenzo[b,d]oxepine-9,2'-[1.3]dioxolane]-3-carboxylate → (7aSR,11aRS)-11a-ethyl-N-(2-methylpyridin-3-yl)-7,7a,8,10,11,11a-hexahydro-6H-spiro[dibenzo[b,d]oxepine-9,2'-[1.3]dioxolane]-3-carboxamide

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0℃; for 0.25h;	100%

2-methyl-3-pyridinamine (3430-10-2) + C21H26O4 → C26H30N2O3

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 20℃; for 0.0833333h;	100%

2-methyl-3-pyridinamine (3430-10-2) + 7-chloro-2-(4-hydroxyphenyl)-pyrido[3,2-d]pyrimidine (1345955-99-8) → 2-(4-hydroxyphenyl)-7-((2-methyl)-pyridin-3-ylamino)-pyrido[3,2-d]pyrimidine (1345956-37-7)

Conditions	Yield
With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; for 1h; Buchwald-Hartwig Coupling; Microwave irradiation;	97%

2-methyl-3-pyridinamine (3430-10-2) + (4a'S,10a'R)-methyl 4a'-benzyl-3',4',4a',10a'-tetrahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate (1400926-96-6) → (4a'S,10a'R)-4a'-benzyl-N-(2-methylpyridin-3-yl)-3',4',4a',10a'-tetrahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxamide (1400926-97-7)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃; for 1.5h; Inert atmosphere;	95%

2-methyl-3-pyridinamine (3430-10-2) + (4bS,7R,8aS)-methyl 4b-benzyl-10-methyl-7-(triethylsilyloxy)-7-(trifluoromethyl)-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxylate (1400927-16-3) → (4bS,7R,8aS)-4b-benzyl-10-methyl-N-(2-methylpyridin-3-yl)-7-(triethylsilyloxy)-7-(trifluoromethyl)-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxamide (1400927-17-4)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;	92%

2-methyl-3-pyridinamine (3430-10-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-(2-methylpyridin-3-yl)carbamate (1219095-87-0)

Conditions	Yield
In tetrahydrofuran at 20℃; for 336h;	90%
In hexane; ethyl acetate at 60℃;	46%
With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 16h;
In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

2-methyl-3-pyridinamine (3430-10-2) + (4bS,8aS)-methyl 4b-benzyl-7-hydroxy-7-(trifluoromethyl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-2-carboxylate (1400926-33-1) → (4bS,8aS)-4b-benzyl-7-hydroxy-N-(2-methylpyridin-3-yl)-7-(trifluoromethyl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-2-carboxamide (1400926-34-2)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 20℃; for 2h;	90%

2-methyl-3-pyridinamine (3430-10-2) + (4bR,7R,8aR)-4b-benzyl-7-hydroxy-6-oxo-7-phenyl-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-2-carboxylic acid (1206877-03-3) → (4bR,7R,8aR)-4b-benzyl-7-hydroxy-N-(2-methylpyridin-3-yl)-6-oxo-7-phenyl-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-2-carboxamide (1206877-04-4)

Conditions	Yield
With 1-methyl-1H-imidazole; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; acetonitrile at 25℃;	89%

2-methyl-3-pyridinamine (3430-10-2) → 3-chloro-2-methylpyridine (72093-03-9)

Conditions	Yield
With hydrogenchloride; nitric acid; trichlorophosphate In water at 20 - 25℃;	89%

2-Amino-6-methylpyridine (1824-81-3) + 2-methyl-3-pyridinamine (3430-10-2) + dmap (1122-58-3) + 2,6-pyridine dicarbonyl dichloride → pyridine-2,6-dicarboxylic acid diamide (4663-97-2)

Conditions	Yield
With triethylamine In dichloromethane	88%
With triethylamine In dichloromethane	88%

2-methyl-3-pyridinamine (3430-10-2) + 4'-chloro-2-phenylacetophenone (1889-71-0) → 1-(4-((2-methylpyridin-3-yl)amino)phenyl)-2-phenylethanone (1501945-32-9)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; cis-[1,1'-bis(diphenylphosphino)ferrocene](2-methylphenyl)nickel(II) chloride; acetonitrile In tert-butyl alcohol at 110℃; for 16h; Inert atmosphere; Molecular sieve;	87%

2-methyl-3-pyridinamine (3430-10-2) + rac-methyl (4S,7R)-7-((((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepine-4-yl)-3-methylbenzoate → rac-4-((4S,7R)-(7-((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methyl-N-(2-methylpyridin-3-yl)benzamide

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Cooling;	85%

2-methyl-3-pyridinamine (3430-10-2) + (4bS,7R,8aS)-methyl 4b-benzyl-7-hydroxy-7-(trifluoromethyl)-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxylate (1400927-12-9) → (4βS,7R,8αS)-4β-benzyl-7-hydroxy-N-(2-methylpyridin-3-yl)-7-(trifluoromethyl)-4β,5,6,7,8,8α-hexahydrophenanthrene-2-carboxamide (1044589-16-3)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃; for 1.5h;	83%

2-methyl-3-pyridinamine (3430-10-2) + (4bS,7R,8aR)-methyl 4b-benzyl-7-ethyl-7-hydroxy-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxylate (1400927-02-7) → (4bS,7R,8aR)-4b-benzyl-7-ethyl-7-hydroxy-N-(2-methylpyridin-3-yl)-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxamide (1400927-03-8)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃; for 0.833333h; Inert atmosphere;	82%

2-methyl-3-pyridinamine (3430-10-2) + (7aSR,9SR,11aRS)-11a-ethyl-9-hydroxy-9-(3,3,3-trifluoro-propyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid methyl ester → (7aSR,9SR,11aRS)-11a-ethyl-9-hydroxy-9-(3,3,3-trifluoro-propyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 20℃; for 0.0833333h;	82%

2-methyl-3-pyridinamine (3430-10-2) + phthalic anhydride (85-44-9) → 2-(2-methylpyridin-3-yl)isoindoline-1,3-dione

Conditions	Yield
With acetic acid at 100℃; Inert atmosphere;	82%

2-methyl-3-pyridinamine (3430-10-2) + (4bRS,7RS,8aRS)-methyl 4b-ethyl-7-propyl-7-hydroxy-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxylate → (4bRS,7RS,8aRS)-4b-ethyl-7-propyl-7-hydroxy-N-(2-methylpyridin-3-yl)-4b,5,6,7,8,8a-hexahydrophenanthrene-2-carboxamide

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃; for 1.5h; Inert atmosphere;	74%

2-methyl-3-pyridinamine (3430-10-2) + Phenyl N-phenylphosphoramidochloridate (51766-21-3) → phenyl N-(2-methylpyridin-3-yl)-N'-phenylphosphorodiamidate

Conditions	Yield
With N,N'-dimethylpiperazine In tetrahydrofuran at 30 - 50℃; for 4h;	74%

2-methyl-3-pyridinamine (3430-10-2) + C8H7ClINO → 1-(2-iodophenyl)-1-methyl-3-(2-methylpyridin-3-yl)urea

Conditions	Yield
Stage #1: 2-methyl-3-pyridinamine With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C8H7ClINO In tetrahydrofuran at -78 - 20℃; for 2h;	71%

2-methyl-3-pyridinamine (3430-10-2) + N-(benzyloxycarbonyl)succinimide (75315-63-8) → 3-(N-benzyloxycarbonyl)-2-methylpyridine (177559-93-2)

Conditions	Yield
In N,N-dimethyl-formamide for 48h;	68%
In N,N-dimethyl-formamide for 48h;	68%

2-methyl-3-pyridinamine (3430-10-2) + 5-bromo-2-methyl-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide (899897-86-0) → 2-Methyl-5-(2-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide

Conditions	Yield
With caesium carbonate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100 - 150℃; for 0.5h; Microwave irradiation;	68%

2-methyl-3-pyridinamine (3430-10-2) + (4βS,7R,8αR)-methyl 4β-benzyl-7-(bis(benzyloxy)phosphoryloxy)-7-(trifluoromethyl)-4β,5,6,7,8,8α,9,10-octahydrophenanthrene-2-carboxylate (1044535-54-7) → dibenzyl (2R,4αS,10αR)-4α-benzyl-7-((2-methylpyridin-3-yl)carbamoyl)-2-(trifluoromethyl)-1,2,3,4,4α,9,10,10α-octahydrophenanthren-2-ylphosphate (1044535-56-9)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 10℃; for 0.5h; Product distribution / selectivity;	68%

2-methyl-3-pyridinamine (3430-10-2) → 3-fluoro-2-methylpyridine

Conditions	Yield
With tetrafluoroboric acid; ethyl nitrite Balz-Schiemann reaction;	66%
Stage #1: 2-methyl-3-pyridinamine With phosphoric acid In tert-butyl alcohol Balz-Schiemann Reaction; Inert atmosphere; Stage #2: With tert.-butylnitrite; potassium phenyltrifluoborate In tert-butyl alcohol at 20 - 50℃; for 2.33333h; Balz-Schiemann Reaction; Inert atmosphere; Stage #3: With 2,4-Dinitrofluorobenzene In dimethylsulfoxide-d6; tert-butyl alcohol at 20℃; Inert atmosphere;	35 %Spectr.

2-methyl-3-pyridinamine (3430-10-2) + acetic anhydride (108-24-7) → 1-(1H-pyrazolo[4,3-b]pyridin-1-yl)-ethan-1-one (52090-62-7)

Conditions	Yield
Stage #1: 2-methyl-3-pyridinamine; acetic anhydride In chloroform at 0 - 20℃; Stage #2: With potassium acetate; isopentyl nitrite In chloroform Reflux;	65%

Upstream product

• 1260000-13-2 2-methyl-3-pyridyl tosylate 
• 28489-45-4 6-methyl-5-nitropyridin-2-ol 
• 1824-81-3 2-Amino-6-methylpyridine 
• 18699-87-1 2-methyl-3-nitropyridine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 22280-62-2 6-methyl-5-nitro-2-pyridinamine 
• 80352-62-1 2-bis(benzyloxycarbonyl)methyl-3-nitropyridine 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 13061-96-6 dihydroxy-methyl-borane 
• 80352-63-2 3-aminopyridine-2-acetic acid 
• 76809-24-0 2,2-dimethyl-3-(2-methylpyrid-3-yl)-4-oxo-4H-1,3-benzoxazine 
• 22280-60-0 6-chloro-4-methyl-3-nitropyridine 
• 58539-65-4 2-methylnicotinamide 

Downstream Products

• 116286-64-7 N-(2-methyl-[3]pyridyl)-formamide 
• 65052-85-9 N-(pyridin-2-yl)-N-methylbenzamide 
• 160590-37-4 (2-methyl-[3]pyridyl)-hydrazine 
• 18699-87-1 2-methyl-3-nitropyridine 
• 126325-47-1 3-amino-6-bromo-2-methylpyridine 
• 126325-48-2 3-amino-4-bromo-2-methylpyridine 
• 177559-93-2 3-(N-benzyloxycarbonyl)-2-methylpyridine 
• 34050-39-0 N-(2-methyl-pyridin-3-yl)-acetamide 
• 113209-81-7 3-fluoro-2-methylpyridine 1-oxide 
• 471909-54-3 3-fluoropyridine-2-carbaldehyde oxime 
• 31224-43-8 3-fluoropyridine-2-carbaldehyde 
• 15931-15-4 3-fluoro-2-methylpyridine 
• 1501945-32-9 1-(4-((2-methylpyridin-3-yl)amino)phenyl)-2-phenylethanone 
• 72093-03-9 3-chloro-2-methylpyridine 

Relevant articles and documents

Reduction of 2-amino-3- and -5-nitropyridine derivatives with hydrazine hydrate

The reactions of 2-amino-3-nitropyridine and 2-amino-5-nitropyridine with hydrazine hydrate resulted in elimination of the amino group and reduction of the nitro group with formation of 3-aminopyridine. A probable reaction mechanism involves addition of hydrazine hydrate at the N-C2 bond, followed by elimination of ammonia and reduction of the nitro group to amino. 2-Amino-4-methyl-3-nitropyridine and 2-amino-5-methyl-3-nitropyridine reacted with hydrazine hydrate in a similar way.

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PYRAZOLE COMPOUND AND MEDICINAL COMPOSITION CONTAINING THE SAME

The present invention provides a novel compound having an excellent JNK inhibitory effect. That is, it provides a compound represented by the following formula, a salt thereof or a hydrate of them. Wherein R1 designates -(CO)h-(NRa)j-(CRb=CRc)k-Ar (wherein Ra, Rb and Rc each independently designate a hydrogen atom, a halogen atom, hydroxyl group, an optionally substituted C1-6 alkyl group or the like; Cy designates a 5- or 6-membered heteroaryl; and V each independently designate the formula -L-X-Y (wherein L designates a single bond, an optionally substituted C1-6 alkylene group or the like; X designates a single bond or the formula -A- (wherein A designates NR2, O, CO, S, SO or SO2) and so on; and Y designates a hydrogen atom, a halogen atom, nitro group or the like).