Ethyl 2-methylnicotinate Chemical Properties

Melting point:

146-147 °C

Boiling point:

126-127 °C24 mm Hg(lit.)

Density 

1.072 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.505(lit.)

Flash point:

217 °F

storage temp. 

Inert atmosphere,Room Temperature

pka

4.02±0.10(Predicted)

form 

Liquid

color 

Clear colorless to orange

Water Solubility 

Slightly soluble in water.

λmax

268nm(EtOH)(lit.)

BRN 

118200

InChI

InChI=1S/C9H11NO2/c1-3-12-9(11)8-5-4-6-10-7(8)2/h4-6H,3H2,1-2H3

InChIKey

TZORNSWZUZDUCU-UHFFFAOYSA-N

SMILES

C1(C)=NC=CC=C1C(OCC)=O

CAS DataBase Reference

1721-26-2(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 2-methylnicotinate(1721-26-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29333990

Storage Class

10 - Combustible liquids

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl 2-methylnicotinate Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Ethyl 2-methylpyridine-3-carboxylate was used in the preparation of amino esters such as ethyl 2(piperidinylaminomethyl)benzoate, ethyl 2-(N-benzyl-N-methylaminomethyl)benzoate, ethyl 2-(diethylaminomethyl)benzoate.

Synthesis

A method for the preparation of Ethyl 2-methylnicotinate, as follows:

(1) 2.0 mol of 1,1,3,3-tetramethoxypropane was added into a reactor at room temperature, 2.5 mol of hydrochloric acid at a mass concentration of 20% was added with stirring, and the reaction was carried out at a controlled temperature of 40?? C. for 4 hours; the 2.5 mol refers to the molar amount of HCl in the hydrochloric acid, and the following is the same;

( 2) adding 1 mol of ??-aminocrotonic acid methyl ester, 6 mol of methanol to the reactor, controlling the reaction temperature at 50??C, and reacting for 6 hours;

wherein the molar ratio of ??-aminocrotonic acid methyl ester, 1,1,3,3-tetramethoxypropane, hydrochloric acid, and methanol was 1.0:2.0:2.5:6.0;

(3) reducing pressure and concentrating the above reaction solution (3)Concentrate the above reaction solution under reduced pressure, neutralize the concentrated solution with 10% aqueous sodium hydroxide solution to the system pH=5.0, add 5 times the mass of ??-aminocrotonic acid methyl ester of ethyl acetate to the system, extract the fractional phase, add 4 times the mass of ??-aminocrotonic acid methyl ester of water to the organic phase, wash the fractional phase, concentrate the organic phase, and then continue to distil with a small rotary-vane vacuum pump to collect the fractions, to obtain the liquid of 2-methyl nicotinic acid methyl ester 105.9 g , with a yield of 70.1% and a purity of 98.45%.

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