103-74-2

Basic information

• Product Name: 2-(2-Hydroxyethyl)pyridine
• Synonyms: 2-ETHANOLPYRIDINE;2-(B-HYDROXYETHYL)PYRIDINE;2-PYRIDINEETHANOL;2-PYRIDYLETHANOL;2-PYRIDIN-2-YL-ETHANOL;2-(2'-HYDROXYETHYL)PYRIDINE;2-(2-HYDROXYETHYL)PYRIDINE;2-(2-PYRIDYL)ETHANOL
• CAS NO: 103-74-2
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• EINECS: 203-140-2
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Amino Acid Derivatives;Aromatics, Heterocycles, Intermediates, Metabolites & Impurities
• Mol File: 103-74-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: -8--7°C
• Boiling Point: 114-116 °C9 mm Hg(lit.)
• Flash Point: 199 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.093 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: n20/D 1.537(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in Chloroform (Slightly), Methanol (Slightly).
• PKA: 14.49±0.10(Predicted)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 111205
• CAS DataBase Reference: 2-(2-Hydroxyethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Hydroxyethyl)pyridine(103-74-2)
• EPA Substance Registry System: 2-(2-Hydroxyethyl)pyridine(103-74-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 2
• RTECS: UT2970450
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 103-74-2(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to brown liquid

Uses

Different sources of media describe the Uses of 103-74-2 differently. You can refer to the following data:
1. 2-Pyridineethanol is a metabolite of the anti-vertigo drug Betahistine (B324000).
2. 2-(2-Hydroxyethyl)pyridine is a metabolite of the anti-vertigo drug Betahistine. It acts as a reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. It is used for carboxyl protection of amino acids. It is also used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. It was used to prepare mononuclear nickel(II) acetate.

General Description

2-(2-pyridyl)ethanol derivatives react with the aryl and alkenyl chlorides (palladium-catalyzed reactions) that result in the substitution of the chloro moieties with a 2-pyridylmethyl group.

InChI:InChI=1/C7H9NO/c9-6-4-7-3-1-2-5-8-7/h1-3,5,9H,4,6H2

Synthetic route

C14H29NO2Si3 → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With potassium hydrogen difluoride; dihydrogen peroxide In tetrahydrofuran; methanol at 50℃; for 24h; Fleming-Tamao Oxidation;	80%

α-picoline (109-06-8) + 1-Hydroxymethyl-1H-benzotriazole (28539-02-8) → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
Stage #1: α-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: 1-Hydroxymethyl-1H-benzotriazole In tetrahydrofuran at -78℃; for 2h;	65%

2-(hydroxyethyl)pyridine-N-oxide (64364-85-8) → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With tetraethylammonium hexafluorophosphate In water; acetonitrile at 80℃; Inert atmosphere; Electrolysis;	63%

2-chloromethylpyridine (4377-33-7) + formaldehyd (50-00-0) → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
Stage #1: 2-chloromethylpyridine With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 70℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran at 70℃; for 6h; Schlenk technique; Inert atmosphere;	59%

α-picoline (109-06-8) + formaldehyd (50-00-0) → 2-vinylpyridine (100-69-6) + 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With sulfuric acid; water; hydrogen at 160℃;

α-picoline (109-06-8) + formaldehyd (50-00-0) → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With water at 120 - 135℃;
With water at 120℃; im geschlossenem Gefaess;
With water at 150℃; im geschlossenem Gefaess;

α-picoline (109-06-8) + formaldehyd (50-00-0) → 2-(2-Hydroxyethyl)pyridine (103-74-2) + 2-(pyridin-2-yl)propane-1,3-diol (49745-42-8)

Conditions	Yield
With potassium hydroxide; water at 130 - 136℃; under 7355.08 Torr;

ethyl 2-(pyridinyl-2)acetate (2739-98-2) → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

β--trimethylene oxide → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With hydrogenchloride

α-picoline (109-06-8) + gaseous formaldehyde → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With phenyllithium anfangs unter Kuehlung, zuletzt bei Siedetemperatur;

2-acetylpyridine (1122-62-9) + RuCl{η6-p-cymene}{η2-(1S,2R)-N-(4-biphenylmethyl)-norephedrine)} + potassium isopropoxide (6831-82-9) → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
In 2-methyl-propan-1-ol; isopropyl alcohol

C11H14F3NO2Si → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; water at 40℃; for 2h; Fleming-Tamao Oxidation;

C9H15NOSi → 2-(2-Hydroxyethyl)pyridine (103-74-2)

Conditions	Yield
With potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; water at 40℃; for 2h; Fleming-Tamao Oxidation;

2-(2-Hydroxyethyl)pyridine (103-74-2) + methanesulfonyl chloride (124-63-0) → 2-(pyridin-2-yl)ethyl methanesulfonate (138428-37-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h;	100%
With triethylamine In acetonitrile at 40℃; under 2585.81 Torr; for 0.333333h; Flow reactor;	100%
With triethylamine In dichloromethane at 25℃; for 3.25h; Cooling with ice;	98%

2-(2-Hydroxyethyl)pyridine (103-74-2) + acetic anhydride (108-24-7) → 2-methylamino-6-(2-hydroxyethyl)pyridine (16632-09-0)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran Inert atmosphere; Glovebox;	100%
With dmap; N-ethyl-N,N-diisopropylamine at 20℃; for 0.516667h; Inert atmosphere; Glovebox;	822 mg

2-(2-Hydroxyethyl)pyridine (103-74-2) + 3-Phenylpropionic acid (501-52-0) → 2-(pyridin-2-yl)ethyl 3-phenylpropanoate

Conditions	Yield
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;	99%

2-(2-Hydroxyethyl)pyridine (103-74-2) + nickel(II) chloride dihydrate → [Ni(μ-Cl)(2-(pyridin-2-yl)ethanol)]2Cl2

Conditions	Yield
Stage #1: nickel(II) chloride dihydrate In 1,2-dimethoxyethane for 1.5h; Reflux; Inert atmosphere; Schlenk technique; Stage #2: In dichloromethane Inert atmosphere; Schlenk technique; Stage #3: 2-(2-Hydroxyethyl)pyridine In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;	96%

2-(2-Hydroxyethyl)pyridine (103-74-2) + trichloroacetonitrile (545-06-2) → 2-(pyridin-2-yl)ethyl 2,2,2-trichloroacetimidate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane	96%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 12h;	79%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 16h;	69%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃;

2-(2-Hydroxyethyl)pyridine (103-74-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-<(2-tert-butyldimethylsilyloxy)ethyl>pyridine (161227-19-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;	96%

2-(2-Hydroxyethyl)pyridine (103-74-2) → 2-(2-Bromoethyl)pyridine hydrobromide (72996-65-7)

Conditions	Yield
With hydrogen bromide	95%
With hydrogen bromide In acetic acid at 78℃; for 48h;	73%
With hydrogen bromide In water; toluene at 120℃;	66%

2-(2-Hydroxyethyl)pyridine (103-74-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-<(2-tert-butyldimethylsilyloxy)ethyl>pyridine (161227-19-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 24h;	95%

2-(2-Hydroxyethyl)pyridine (103-74-2) + trimethylindium diethyl ether adduct (859439-31-9) → [Me2In(2-(2-hydroxyethyl)pyridine-H)]n

Conditions	Yield
In benzene byproducts: CH4, Et2O; under N2; by the react. of In-contg. compd. with a ligand in 1:1 stoich.ratio in benzene; stirring for 4 h at room temp.; the solvent was removed under reduced pressure; recrystn. from benzene/hexane; elem. anal.;	95%

2-(2-Hydroxyethyl)pyridine (103-74-2) + triethylindium diethyl ether adduct → [Et2In(2-(2-hydroxyethyl)pyridine-H)]n

Conditions	Yield
In benzene byproducts: C2H6, Et2O; under N2; by the react. of In-contg. compd. with a ligand in 1:1 stoich.ratio in benzene; stirring for 4 h at room temp.; the solvent was removed under reduced pressure; recrystn. from benzene/hexane; elem. anal.;	95%

2-(2-Hydroxyethyl)pyridine (103-74-2) → [2-(2-CH2CH2OH)PyH][B5O6(OH)4]

Conditions	Yield
With boric acid In methanol; water	95%

2-(2-Hydroxyethyl)pyridine (103-74-2) + boric acid (11113-50-1) → [2-(2-CH2CH2OH)PyH][B5O6(OH)4]

Conditions	Yield
In methanol; water to soln. H3BO3 in aq. MeOH (1:1) amine was added, stirred for 10 min, solvent was removed in vacuo, residue was heated in oven to dry 4 h at 100°C; elem. anal.;	95%

2-(2-Hydroxyethyl)pyridine (103-74-2) + 4-chloro-2-methylquinoline (4295-06-1) → 2-methyl-4-[2-(pyridin-2-yl)ethoxy]quinoline

Conditions	Yield
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; caesium carbonate In toluene at 90℃; for 16h; Glovebox; Inert atmosphere;	95%

2-(2-Hydroxyethyl)pyridine (103-74-2) + O-acetylsalicyloyl chloride (5538-51-2) → acetylsalicylic acid-(2-pyridin-2-yl)ethyl ester hydrochloride

Conditions	Yield
In ethyl acetate at 20℃; for 2h;	94.3%

naphthalen-1-yl-acetyl chloride (5121-00-6) + 2-(2-Hydroxyethyl)pyridine (103-74-2) → 2-(pyridin-2-yl)ethyl 2-(naphthalen-1-yl)acetate

Conditions	Yield
Stage #1: naphthalen-1-yl-acetyl chloride; 2-(2-Hydroxyethyl)pyridine In ethyl acetate; toluene at 20℃; for 2h; Stage #2: With sodium carbonate In dichloromethane; water at 20℃;	94.2%

2-(2-Hydroxyethyl)pyridine (103-74-2) + t-Boc-L-valine (13734-41-3) → (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 2-pyridin-2-yl-ethyl ester (91841-65-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane 1) -20 degC, 10 min.; 2) 20 degC, 3 h;	94%

2-(2-Hydroxyethyl)pyridine (103-74-2) + triethylgallium diethyl ether adduct (31121-29-6) → [Et2Ga(OCH2CH2(C5H4N))]

Conditions	Yield
In benzene byproducts: C2H6, Et2O; under N2; a soln. of a ligand in benzene was added to a benzene soln. ofGa-contg. compd. and stirred for 24 h; the solvent was removed under reduced pressure; elem. anal.;	94%

2-(2-Hydroxyethyl)pyridine (103-74-2) + 2-fluoro-4-bromobenzoic acid (112704-79-7) → 2-(2-pyridyl)ethyl 4-bromo-2-fluorobenzoate (920270-28-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Product distribution / selectivity;	93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; Product distribution / selectivity;	80%

2-(2-Hydroxyethyl)pyridine (103-74-2) + triethylgallium diethyl ether adduct (31121-29-6) → [EtGa(OCH2CH2(C5H4N))2]

Conditions	Yield
In benzene byproducts: C2H6, Et2O; under N2; a soln. of a ligand in benzene was added to a benzene soln. ofGa-contg. compd. and stirred for 24 h; the solvent was removed under reduced pressure; elem. anal.;	93%

2-(2-Hydroxyethyl)pyridine (103-74-2) + trimethylgallium etherate → [MeGa(OCH2CH2(C5H4N))2]

Conditions	Yield
In benzene byproducts: CH4, Et2O; under N2; a soln. of a ligand in benzene was added to a benzene soln. ofGa-contg. compd. and stirred for 24 h; the solvent was removed under reduced pressure; elem. anal.;	93%

2-(2-Hydroxyethyl)pyridine (103-74-2) + N-methyl-2-thiocyanatopyridinium iodide → C8H8N2S (1353778-05-8)

Conditions	Yield
at 90℃; for 0.0833333h; Neat (no solvent); Grinding;	93%

2-(2-Hydroxyethyl)pyridine (103-74-2) + sorbinyl chloride (2614-88-2) → 2-(pyridin-2-yl)ethyl sorbate hydrochloride

Conditions	Yield
With acetic acid In ethyl acetate at 20℃; for 2h; Inert atmosphere;	92.9%

2-(2-Hydroxyethyl)pyridine (103-74-2) + Cinnamoyl chloride (102-92-1) → pyridiniumethyl ester cinnamic acid hydrochloride

Conditions	Yield
With acetic acid In ethyl acetate at 20℃; for 2h;	92.1%

2-(2-Hydroxyethyl)pyridine (103-74-2) + Z-Leu-OH (2018-66-8) → (S)-2-Benzyloxycarbonylamino-4-methyl-pentanoic acid 2-pyridin-2-yl-ethyl ester (91841-60-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane 1) -20 degC, 10 min.; 2) 20 degC, 3 h;	92%

2-(2-Hydroxyethyl)pyridine (103-74-2) + trimethylgallium etherate → [Me2Ga(OCH2CH2(C5H4N))]

Conditions	Yield
In benzene byproducts: CH4, Et2O; under N2; a soln. of a ligand (5.03 mmol) in benzene was added dropwise to a benzene soln. of Ga-contg. compd. (5.03 mmol) and stirred for 24 h; the solvent was removed under reduced pressure; elem. anal.;	92%

2-(2-Hydroxyethyl)pyridine (103-74-2) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 2-(2-pyridyl)ethyl 4-bromo-3-methylbenzoate (920270-48-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	92%

2-(2-Hydroxyethyl)pyridine (103-74-2) + C22H24N2O6S (1456807-88-7) → 4-methyl-3-(4-methylpiperazin-1-yl)-2-oxo-5-(2-(pyridin-2-yl)ethoxy)-2H-chromen-7-yl 4-methylbenzenesulfonate (1456808-51-7)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 0.333333h; Mitsunobu Displacement;	91%

2-(2-Hydroxyethyl)pyridine (103-74-2) + diclofenac sodium (15307-79-6) + copper(II) acetate monohydrate (6046-93-1) → C42H36Cl4Cu2N4O6

Conditions	Yield
In methanol at 50℃;	91%

2-(2-Hydroxyethyl)pyridine (103-74-2) + nickel(II) sulfate hexahydrate → [NiII(2-(2-hydroxylethyl)pyridine)(H2O)4]SO4

Conditions	Yield
In methanol at 24.84℃; for 6h;	91%

2-(2-Hydroxyethyl)pyridine (103-74-2) + p-toluenesulfonyl chloride (98-59-9) → 2-(2-tosylethyl)pyridine (107516-54-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 24h; Inert atmosphere; Schlenk technique;	91%

Upstream product

• 4377-33-7 2-chloromethylpyridine 
• 50-00-0 formaldehyd 
• 64364-85-8 2-(hydroxyethyl)pyridine-N-oxide 
• 1122-62-9 2-acetylpyridine 
• 6831-82-9 potassium isopropoxide 
• 109-06-8 α-picoline 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 

Downstream Products

• 261360-86-5 phenyl 2-(2-pyridyl)ethyl ether 
• 1484-80-6 2-ethylpiperidine 
• 322732-72-9 5'-O-(monomethoxytrityl)thymidine 3'-[2,5-dichlorophenyl 2-(pyridin-2-yl)ethyl phosphate] 
• 485823-55-0 methyl 2-[(2,4-dichlorobenzoyl)amino]-5-[2-(2-pyridinyl)ethoxy]benzoate 
• 98-98-6 2-Picolinic acid 
• 13115-43-0 2-pyridineacetic acid 
• 357288-91-6 2-Amino-4-(2-methoxy-phenyl)-6-(2-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile 
• 85002-52-4 4-<2-(2-pyridyl)ethoxy>nitrobenzene 
• 408365-81-1 N-{4-[2-(2-pyridinyl)ethoxy]phenyl}-4'-(trifluoromethyl)-1,1'-biphenyl-2-carboxamide 
• 408366-47-2 N-{3-Nitro-4-[2-(2-pyridinyl)ethoxy]phenyl}-4'-(trifluoromethyl)-1,1'-biphenyl-2-carboxamide 
• 408365-76-4 4'-methyl-N-(4-{[2-(2-pyridinyl)ethyl]amino}phenyl)-1,1'-biphenyl-2-carboxamide 
• 1201582-30-0 5-acetyl-7-[3-(4-fluorophenyl)butoxy]-4-methyl-6-(2-pyridin-2-ylethoxy)-2-trifluoromethylbenzo[d]oxazole 
• 1025014-77-0 3-(phenylethynyl)-2-(2-(pyridin-2-yl)ethoxy)pyrido[3,2-b]pyrazine 
• 99584-01-7 6-(2-hydroxyethyl)pyridine-2-carbonitrile 

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