583-61-9

Basic information

• Product Name: 2,3-Lutidine
• Synonyms: 2,3-DIMETHYLPYRIDINE(2,3-LUTIDINE);a,b-Dimethylpyridine;2,3-Lutidine (8CI);Pyridine, 2,3-dimethyl- (9CI);2,3-Lutidine, 98+% 100ML;2,3- twoMethylpyridine;2,3-Lutidine 99%;LUT
• CAS NO: 583-61-9
• Molecular Formula: C₇H₉N
• Molecular Weight: 107.15
• EINECS: 209-514-1
• Product Categories: Pyridines derivates;Heterocyclic Compounds;Biochemistry;Reagents for Oligosaccharide Synthesis
• Mol File: 583-61-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: −15 °C(lit.)
• Boiling Point: 162-163 °C(lit.)
• Flash Point: 122 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.945 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.01E-12mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• Storage Temp.: Flammables area
• PKA: 6.57(at 25℃)
• Water Solubility: 95 g/L (26 ºC)
• BRN: 106418
• CAS DataBase Reference: 2,3-Lutidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Lutidine(583-61-9)
• EPA Substance Registry System: 2,3-Lutidine(583-61-9)

Safety Data

• Hazard Codes: Xn,F,Xi
• Statements: 10-22-37/38-41-20/21/22-36/37/38
• Safety Statements: 16-26-39-36/37-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 583-61-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

2,3-Lutidine is a lansoprazole intermediates. It is used as pharmaceutical intermediate.

Purification Methods

Steam distil it from a solution containing about 1.2 equivalents of 20% H2SO4, until ca 10% of the base has been carried over with the non-basic impurities. The acidic solution is then made alkaline, and the base is separated, dried over NaOH or BaO, and fractionally distilled. The distilled lutidine is converted to its urea complex by stirring 100g with 40g of urea in 75mL of H2O, cooling to 5o, filtering at the pump, and washing with 75mL of H2O. The complex, dissolved in 300mL of H2O, is steam distilled until the distillate gives no turbidity with a little solid NaOH. The distillate is then treated with excess solid NaOH, and the upper layer is removed: the aqueous layer is then extracted with diethyl ether. The upper layer and the ether extract are combined, dried (K2CO3), and distilled through a short column. Final purification is by fractional crystallisation using partial freezing. The picrate crystallises from EtOH with m 187-188o. [Kyte et al. J Chem Soc 4454 1960, Beilstein 20 H 243, 20 II 159, 20 III/IV 2765, 20/6 V 15.]

InChI:InChI=1/C22H17IN2/c23-21-24-16-17-25(21)22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

Synthetic route

2-Methyl-3-acetoxymethylpyridin (87851-05-6) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With hydrogen; Pd-BaSO4 In ethanol for 0.5h; Ambient temperature;	99.2%

N-(3-methyl-2-methyl-2H-pyridin-1-yl)-N-methyl-benzamidine → 2,3-Lutidine (583-61-9)

Conditions	Yield
Stage #1: N-(3-methyl-2-methyl-2H-pyridin-1-yl)-N-methyl-benzamidine With manganese triacetate; acetic acid at 60℃; for 2h; Stage #2: With water; acetic acid at 80℃;	81%

5-chloro-5,6-dimethyl-2,3,4,5-tetrahydropyridine (326893-28-1) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran Heating;	80%

butanone (78-93-3) → 2,3-Lutidine (583-61-9) + 2,3,6-trimethylpyridine (1462-84-6) + 2,3,4-lutidine (2233-29-6)

Conditions	Yield
With ammonia; chromium(III) oxide; aluminium at 350℃;	A 30.7% B 46.2% C 23%

butanone (78-93-3) → 2,6-dimethylpyridine (108-48-5) + 2,3-Lutidine (583-61-9) + 2,3,6-trimethylpyridine (1462-84-6) + 2,3,4-lutidine (2233-29-6)

Conditions	Yield
With ammonia; chromium(III) oxide; aluminium at 375℃;	A 6.8% B 24.6% C 45.4% D 25.7%
With ammonia; chromium(III) oxide; aluminium at 425℃;	A 25.3% B 34.5% C 13.8% D 13.8%
With ammonia; chromium(III) oxide; aluminium at 450℃;	A 21.8% B 22.4% C 29.4% D 11.7%
With ammonia; chromium(III) oxide; aluminium at 300 - 450℃; Product distribution;

3-Methylpyridine (108-99-6) → pyridine (110-86-1) + α-picoline (109-06-8) + 2,3-Lutidine (583-61-9) + 2,4-lutidine (108-47-4) + 2,5-dimethylpyridine (589-93-5)

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 330℃; under 750.06 Torr; Product distribution;	A 0.3% B 0.5% C 5.3% D 8% E 30.9%

formaldehyd (50-00-0) + acetaldehyde (75-07-0) + acetone (67-64-1) → 2,3-Lutidine (583-61-9) + 3-ethylpyridine (536-78-7) + 2,3,4-lutidine (2233-29-6) + 3-Methylpyridine (108-99-6)

Conditions	Yield
With diammonium phosphate In ethanol; water at 234℃; for 1h;	A 25% B 8% C 13% D 22%

α-picoline (109-06-8) → pyridine (110-86-1) + 2,6-dimethylpyridine (108-48-5) + 2,3-Lutidine (583-61-9) + 2,5-dimethylpyridine (589-93-5)

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 330℃; under 750.06 Torr; Product distribution;	A 14.9% B 11.4% C 3% D 1.6%

5,6-dimethyl-1,2,3,4-tetrahydro-pyridine (412320-62-8) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With magnesium hydrosilicate; hydrogen; palladium at 280℃;

6-chloro-2,3-dimethylpyridine (72093-13-1) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With ethanol; palladium Hydrogenation;

1-Methyl-3-acetylpiperidine (91324-25-3) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With selenium at 300℃;

4,6-dichloro-2,3-dimethyl-pyridine (101252-84-0) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With methanol; potassium acetate; palladium Hydrogenation;

2,3-bis(chloromethyl)-pyridine (45754-12-9) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With methanol; palladium on activated charcoal; Lindlar's catalyst Hydrogenation;

methanol (67-56-1) + 3-Methylpyridine (108-99-6) + lead(IV) tetraacetate (546-67-8) + acetic acid (64-19-7) → 2,3-Lutidine (583-61-9) + 2,5-dimethylpyridine (589-93-5)

Conditions	Yield
at 110℃;

4-methyl-5-oxohexanal (68208-68-4) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With ethanol; water; hydroxylamine anschliessend Erwaermen mit wss. Salzsaeure;

5,6-dimethyl-1,2,3,4-tetrahydro-pyridine; hydrochloride → 2,3-Lutidine (583-61-9)

Conditions	Yield
bei der Zinstaub-Destillation;

allyl alcohol (107-18-6) + butanone (78-93-3) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With ammonia at 400℃; Leiten ueber mit Cadmiumphosphat impraegnierte Fullererde;

2.3-dimethyl-pyridine-carboxylic acid-(5) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With methyllithium; calcium carbonate bei der Destillation;

hydrochloride of 2.3-dimethyl-1.4.5.6-tetrahydro-pyridine → 2,3-Lutidine (583-61-9)

Conditions	Yield
With zinc durch Destillation;

5,6-dimethylpyridine-3-carboxylic acid (757903-81-4) + lime/chalk/ → 2,3-Lutidine (583-61-9)

Conditions	Yield
bei der Destillation;

5,6-dimethyl-1,2,3,4-tetrahydro-pyridine (412320-62-8) + hydrogen + palladium/ asbestos → 2,3-Lutidine (583-61-9)

Conditions	Yield
at 290℃;

1-Methyl-3-acetylpiperidine (91324-25-3) + selenium → 2,3-Lutidine (583-61-9)

Conditions	Yield
at 300℃; unter Druck;

3-methyl-cyclohexanone oxime (4701-95-5) + P2O5 → 2,3-Lutidine (583-61-9) + methyl cyclohexane (82166-21-0) + toluene (108-88-3) + nitrile C6H11+CN

Conditions	Yield
levorotatory 1-methyl-cyclohexane oxime-(3);

ethyl 2-methyl nicotinate (1721-26-2) + methylphenylsilane (766-08-5) → 2,3-Lutidine (583-61-9) + 3-(ethoxy-methyl-phenyl-silanyloxymethyl)-2-methyl-pyridine

Conditions	Yield
With dimethyltitanocene at 20℃; Title compound not separated from byproducts;

3-Methylpyridine (108-99-6) → 2,3-Lutidine (583-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Tf2O / CH2Cl2 / -40 - 20 °C 1.2: 80 percent / CH2Cl2 / -70 °C 2.1: Mn(OAc)3*2H2O; AcOH / 2 h / 60 °C 2.2: 81 percent / H2IO6; AcOH; H2O / 80 °C View Scheme

[2,5-Dichloro-1,2-dimethyl-pent-(E)-ylidene]-isopropyl-amine (121076-19-5) → 2,3-Lutidine (583-61-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 28 percent / NaN3 / dimethylsulfoxide / 20 h / 55 °C 2: 48 percent / SnCl2 / methanol / 5 h / 20 °C 3: 80 percent / KOBu-t / tetrahydrofuran / Heating View Scheme

N-(6-azido-3-chloro-3-methyl-2-hexylidene)isopropylamine → 2,3-Lutidine (583-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / SnCl2 / methanol / 5 h / 20 °C 2: 80 percent / KOBu-t / tetrahydrofuran / Heating View Scheme

(2-methylpyridin-3-yl)methanol (56826-61-0) → 2,3-Lutidine (583-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / 1.) room temp., 15 h, 2.) reflux, 2 h 2: 99.2 percent / H2 / Pd/BaSO4 / ethanol / 0.5 h / Ambient temperature View Scheme

ethyl 2-methyl nicotinate (1721-26-2) → 2,3-Lutidine (583-61-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0.5 h / 40 °C 2: 91 percent / 1.) room temp., 15 h, 2.) reflux, 2 h 3: 99.2 percent / H2 / Pd/BaSO4 / ethanol / 0.5 h / Ambient temperature View Scheme

2,3-Lutidine (583-61-9) → 2,3-dimethylpyridine 1-oxide (22710-07-2)

Conditions	Yield
With sodium tungstate; dihydrogen peroxide In water at 55℃; for 3h; Temperature;	99%
With 3-chloro-benzenecarboperoxoic acid In Isopropyl acetate at 10 - 35℃; for 5.83333h; Green chemistry;	98.9%
With △-Na8H[PW9O34]·19H2O; dihydrogen peroxide In water at 20℃; for 24h; Green chemistry;	94%

2,3-Lutidine (583-61-9) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 2,3-dimethylpiperidine-1-carboxylate

Conditions	Yield
Stage #1: 2,3-Lutidine With chloro(1,5-cyclooctadiene)rhodium(I) dimer; borane-ammonia complex In 2,2,2-trifluoroethanol at 20℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: di-tert-butyl dicarbonate With triethylamine In 2,2,2-trifluoroethanol at 20℃; Inert atmosphere; Schlenk technique; Sealed tube;	99%

2,3-Lutidine (583-61-9) + cobalt pivalate → bis(2,3-dimethylpyridino)tetra(μ2-O,O'-trimethylacetato)dicobalt(II) (1006049-96-2)

Conditions	Yield
In acetonitrile under Ar atm. soln. 2,3-Me2C5H3N in MeCN was added to (Co(Me3CCOO)2)n and strirred at 80°C for 15 min; soln. was concd. at 0.1 Torr and 20°C and allowed to crystallize at 20°C for 12 h, ppt. was washed with cold benzene and dried under Ar stream; elem. anal.;	98%

2,3-Lutidine (583-61-9) + Ni2(μ-H2O)(μ-OOC-tert-Bu)2(OOC-tert-Bu)2(tert-BuCOOH)4 (515845-82-6) → bis(2,3-dimethylpyridino)tetra(μ2-O,O'-trimethylacetato)dinickel(II) (239471-96-6)

Conditions	Yield
In benzene under Ar atm. soln. 2,3-Me2C5H3N in benzene was added to Ni6(Me3CCOO)2)12 and strirred at 70°C for 15 min; soln. was concd. at 0.1 Torr and 20°C and allowed to crystallize at 20°C for 12 h, ppt. was washed with cold benzene and dried under Ar stream; elem. anal.;	98%

2,3-Lutidine (583-61-9) + benzoyl chloride (98-88-4) → 2,3-dimethyl-N-benzoyliminopyridinium ylide (860802-84-2)

Conditions	Yield
Stage #1: 2,3-Lutidine With O-(2,4-dinitrophenyl)hydroxylamine In tetrahydrofuran; water at 40℃; for 12h; Stage #2: benzoyl chloride With sodium hydroxide In tetrahydrofuran at 20℃; for 4h;	96%

2,3-Lutidine (583-61-9) + methyl 2-((tosylimino)methyl)benzoate → 3-((3-methylpyridin-2-yl)methyl)-2-tosylisoindolin-1-one (1218989-13-9)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In α,α,α-trifluorotoluene at 120℃; for 24h; Inert atmosphere; screw-cap vial;	95%

2,3-Lutidine (583-61-9) + 1-hexene (592-41-6) → C13H21N

Conditions	Yield
With triphenylcarbenium tetra(pentafluorophenyl)borate; C63H83N2O2ScSi2 In toluene at 40℃; for 48h; Schlenk technique; Inert atmosphere; enantioselective reaction;	95%

2,3-Lutidine (583-61-9) + tert-butyl (E)-cinnamyl carbonate (95932-32-4) → C16H17N

Conditions	Yield
Stage #1: 2,3-Lutidine With boron trifluoride diethyl etherate In tetrahydrofuran for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: tert-butyl (E)-cinnamyl carbonate With C49H50IrNO4P(1+)*CF3O3S(1-); lithium hexamethyldisilazane In tetrahydrofuran at 30℃; for 8h; Inert atmosphere; Schlenk technique; enantioselective reaction;	94%

2,3-Lutidine (583-61-9) + 1,5-Hexadien (592-42-7) → C13H19N

Conditions	Yield
With tris(pentafluorophenyl)borate; C42H51N3PSc In chlorobenzene at 100℃; for 8h; diastereoselective reaction;	94%

2,3-Lutidine (583-61-9) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,3-dimethylpyridin-1-ium-1-amine 2,4,6-trimethylbenzenesulfonate (81450-86-4)

Conditions	Yield
In dichloromethane for 0.5h; cooling;	93%

2,3-Lutidine (583-61-9) + trimethylamine-iodoborane → bis(2.3-lutidine)boronium iodide

Conditions	Yield
In not given	93%

2,3-Lutidine (583-61-9) + Bis(acetonitrile-κN)hexakis(μ-O,O'-trimethylacetato)(nitrato-κ2O,O')dizinc(II)europium(III) + acetonitrile (75-05-8) → Bis(2,3-dimethylpyridine-κN)hexakis(μ-O,O'-trimethylacetato)(nitrato-κ2O,O')dizinc(II)europium(III) acetonitrile monosolvate

Conditions	Yield
at 80℃; for 0.333333h;	93%

2,3-Lutidine (583-61-9) + meta-bromotoluene (591-17-3) → 3-methyl-2-(3-methylbenzyl)pyridine (1334723-74-8)

Conditions	Yield
Stage #1: 2,3-Lutidine With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 25℃; for 0.25h; Inert atmosphere; Stage #2: meta-bromotoluene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 1-ethyl-2-pyrrolidinone; palladium diacetate In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;	91%

2,3-Lutidine (583-61-9) + ethyl-3,3,3-trifluoropyruvate (13081-18-0) → ethyl 3,3,3-trifluoro-2-hydroxy-2-(3-methylpyridin-2-ylmethyl)propanoate (1419293-09-6)

Conditions	Yield
With ytterbium(III) triflate In 1,4-dioxane at 90℃; for 12h;	91%
With iron(II) acetate In 1,4-dioxane at 120℃; for 24h; Schlenk technique; Inert atmosphere;	24%

2,3-Lutidine (583-61-9) + cyclohexylallene (5664-17-5) → C16H23N

Conditions	Yield
With (C5Me4SiMe3)Sc(CH2C6H4NMe2-o)2; trityl tetrakis(pentafluorophenyl)borate In toluene at 70℃; for 36h; Glovebox; Schlenk technique; Sealed tube; stereoselective reaction;	91%

2,3-Lutidine (583-61-9) + 5-methyl-indole-2,3-dione (608-05-9) → 3-hydroxy-3-((3-methylpyridin-2-yl)methyl)indolin-2-one (1395322-34-5)

Conditions	Yield
In water for 1h; Reagent/catalyst; Reflux;	91%

2,3-Lutidine (583-61-9) + benzoic acid methyl ester (93-58-3) → C14H13NO

Conditions	Yield
Stage #1: 2,3-Lutidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: benzoic acid methyl ester In tetrahydrofuran; hexane at 0℃; for 3h; Inert atmosphere;	91%

2,3-Lutidine (583-61-9) + styrene (292638-84-7) → C15H17N

Conditions	Yield
With tris(pentafluorophenyl)borate; C42H51N3PSc In chlorobenzene at 100℃; for 9h; Inert atmosphere; Schlenk technique; Glovebox;	91%

2,3-Lutidine (583-61-9) + zinc trimethylacetate → [zinc(II)(μ2-κ1O:κ1O'-O2C(t-Bu))2(2,3-lutidine)]2 (1307949-66-1)

Conditions	Yield
In methanol soln. of C5H3NMe2 in MeOH added to soln. of Zn salt in MeOH, stirred at room temp. for 12 h; volatiles removed under vac., crystd. by diffusing CHCl3 over MeOH soln.at room temp. for 4 d; elem. anal.;	90%

2,3-Lutidine (583-61-9) + 1-bromo-4-methoxy-benzene (104-92-7) → 2-(4-methoxybenzyl)-3-methylpyridine (33399-83-6)

Conditions	Yield
Stage #1: 2,3-Lutidine With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 25℃; for 0.25h; Inert atmosphere; Stage #2: 1-bromo-4-methoxy-benzene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 1-ethyl-2-pyrrolidinone; palladium diacetate In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;	90%

2,3-Lutidine (583-61-9) + 2-oxo-2H-chromene-3-carboxylic acid (531-81-7) → 4-((3-methylpyridin-2-yl)methyl)chroman-2-one (1542158-10-0)

Conditions	Yield
In 1,4-dioxane at 120℃; for 48h;	90%

2,3-Lutidine (583-61-9) + 1-cyanoethyl trifluoromethanesulfonate (1403873-31-3) → 1-(1-cyanoethyl)-2,3-dimethylpyridinium triflate

Conditions	Yield
In diethyl ether at 20℃; for 48h; Inert atmosphere;	90%

2,3-Lutidine (583-61-9) + ethyl 2-bromomethyl-2-propenoate (17435-72-2) → C13H17NO2

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	90%

2,3-Lutidine (583-61-9) + 1-adamantyl bromomethyl ketone (5122-82-7) → 2,3-dimethyl-1-[2-oxo-2-(tricyclo[3.3.1.13,7]dec-1-yl)ethyl]pyridinium bromide

Conditions	Yield
In acetonitrile at 20℃;	90%

2,3-Lutidine (583-61-9) + inden-1-one (83-33-0) → 1-(3-Methylpyridin-2-ylmethyl)-1-indanol

Conditions	Yield
With n-butyllithium	89%

2,3-Lutidine (583-61-9) + Dimethyldisulphide (624-92-0) → 2-bis(methylthio)methyl-3-methylpyridine

Conditions	Yield
Stage #1: 2,3-Lutidine With n-butyllithium; N-ethyl-N,N-diisopropylamine; sodium t-butanolate In tetrahydrofuran; hexane at -78℃; Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78℃; Further stages.;	89%

2,3-Lutidine (583-61-9) + ruthenium(II) phthalocyanine (27636-56-2) → (phthalocyaninato)(2,3-lutidine)2-ruthenium(II) (133776-65-5)

Conditions	Yield
In neat (no solvent) under N2; refluxed for 5 h; addn. of hexane to hot soln.; slowly cooled down to room temp.; filtered; washed (MeOH); chromy. (Al2O3, CHCl3); dried (70°C); elem. anal.; UV; IR;	89%

2,3-Lutidine (583-61-9) + 2-oxo-2H-thiochromene-3-carboxylic acid (66253-08-5) → 4-((3-methylpyridin-2-yl)methyl)thiochroman-2-one (1542158-28-0)

Conditions	Yield
In 1,4-dioxane at 120℃; for 48h;	89%

2,3-Lutidine (583-61-9) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 5,6-dimethylpicolinamide

Conditions	Yield
With dipotassium peroxodisulfate; oxygen; sodium formate; silver nitrate In water at 80℃; for 4h; Schlenk technique; regioselective reaction;	89%
With dipotassium peroxodisulfate; oxygen; sodium acetate; silver nitrate In water at 80℃; for 4h; Green chemistry;	89%

Upstream product

• 91324-25-3 1-Methyl-3-acetylpiperidine 
• 107-18-6 allyl alcohol 
• 78-93-3 butanone 
• 757903-81-4 5,6-dimethylpyridine-3-carboxylic acid 
• 412320-62-8 5,6-dimethyl-1,2,3,4-tetrahydro-pyridine 
• 1721-26-2 ethyl 2-methyl nicotinate 
• 766-08-5 methylphenylsilane 
• 13534-89-9 2,3-dibromopyridine 
• 3430-17-9 2-bromo-3-picoline 
• 74-88-4 methyl iodide 
• 51727-05-0 5,6-dimethyl-2-hydroxynicotinic acid 
• 27992-31-0 5,6-dimethyl-pyridin-2-ol 
• 22428-91-7 2-methyl-3-oxobutanal 
• 90007-21-9 2-hydroxy-5,6-dimethyl-nicotinic acid amide 

Downstream Products

• 55589-47-4 3-methylpyridine-2-carboxaldehyde 
• 60032-57-7 2-methylnicotinaldehyde 
• 365551-66-2 2-(4-methoxy-phenyl)-8-methyl-indolizine 
• 5347-68-2 2,3-dimethylpiperidine 
• 5552-80-7 ethyl 2-(3-methylpyridin-2-yl)acetate 
• 22710-07-2 2,3-dimethylpyridine 1-oxide 
• 4377-43-9 2-chloromethyl-3-methyl-pyridine 
• 97374-30-6 tribromo(2,3-dimethylpyridine)gold(III) 
• 10097-32-2 bromide 
• 27063-90-7 3-bromo-5,6-dimethylpyridine 
• 905273-34-9 5-bromo-2,3-bis (bromomethyl) pyridine 
• 905273-36-1 3-bromo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine 
• 1393546-06-9 3-bromo-6-(tert-butoxycarbonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine 
• 1218989-02-6 4-methyl-N-(2-(3-methylpyridin-2-yl)-1-phenylethyl)benzenesulfonamide 

Relevant articles and documents

Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems

A continuous flow microreactor method for generating and carrying out reactions on pyridyllithiums has been developed based on Br/Li exchange reactions of bromopyridines and dibromopyridines. The reactions can be carried out without using cryogenic conditions by virtue of short residence times and efficient heat transfer, while very low temperatures such as-78 or-110°C are required for conventional batch macro methods. Moreover, sequential introduction of two different electrophiles has been successfully achieved using dibromopyridines in an integrated flow microreactor system composed of four micromixers and four microtube reactors.

Nucleophilic addition to 3-substituted pyridinium salts: Expedient syntheses of (-)-L-733,061 and (-)-CP-99,994

(Chemical Equation Presented) The addition of nucleophiles to 3-substituted pyridinium salts prepared from N-methylbenzamide and various pyridines has been investigated. Good to excellent regioselectivities favoring the 2,3-disubstituted 1,2-dihydropyridines were observed. The resulting 1,2-dihydropyridines led to the corresponding 2,3-disubstituted pyridines upon treatment with Mn(OAc)3/NaIO4. This methodology was also successfully applied to the enantioselective syntheses of (-)-L-733,061 and (-)-CP-99,994, two members of a new class of highly potent, nonpeptide, Substance P antagonists.

Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions

A new synthesis of 2,3-disubstituted pyrroles and pyridines is described. The reaction of 3-halo-1-azaallylic carbanions, regiospecifically generated from α-halogenated ketimines, with ω-iodoazides led to the regiospecific formation of ω-azido-α-haloketimines. Treatment of these functionalized imines with tin(II) chloride afforded halogenated five- and six-membered cyclic imines, which were transformed under mild conditions into 2,3-disubstituted pyrroles and pyridines. The stereoselective reduction of 2,3-dialkyl-3-chloro-1-pyrrolines to afford cis-2,3-dialkyl-3-chloropyrrolidines is also reported.