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Ethyl 2-methylnicotinate

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Ethyl 2-methylnicotinate Basic information
Product Name:Ethyl 2-methylnicotinate
Synonyms:3-Pyridinecarboxylic acid, 2-methyl-, ethyl ester;ETHYL 2-METHYLNICOTINATE;2-METHYLNICOTINIC ACID ETHYL ESTER;Ethyl 2-methylpyridine-3-carboxylate~2-Methylnicotinic acid ethyl ester;ethyl 2-methylpyridine-3-carboxylate;2-Methyl-3-pyridinecarboxylic acid ethyl ester;2-Methylpyridine-3-carboxylic acid ethyl ester;2-methylnicotin ethyl ester
CAS:1721-26-2
MF:C9H11NO2
MW:165.19
EINECS:217-013-4
Product Categories:Esters;Pyridines;Heterocyclic Compounds
Mol File:1721-26-2.mol
Ethyl 2-methylnicotinate Structure
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.)
Fp 217 °F
storage temp. Inert atmosphere,Room Temperature
pka4.02±0.10(Predicted)
form Liquid
color Clear colorless to orange
Water Solubility Slightly soluble in water.
λmax268nm(EtOH)(lit.)
BRN 118200
InChIInChI=1S/C9H11NO2/c1-3-12-9(11)8-5-4-6-10-7(8)2/h4-6H,3H2,1-2H3
InChIKeyTZORNSWZUZDUCU-UHFFFAOYSA-N
SMILESC1(C)=NC=CC=C1C(OCC)=O
CAS DataBase Reference1721-26-2(CAS DataBase Reference)
NIST Chemistry ReferenceEthyl 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 Class10 - Combustible liquids
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Ethyl 2-methylnicotinate Usage And Synthesis
Chemical PropertiesColorless liquid
UsesEthyl 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 50C, 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%.

Ethyl 2-methylnicotinate Preparation Products And Raw materials
Preparation Products3-(ethoxycarbonyl)-2-methylpyridine 1-oxide
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