Nicotinic acid ethyl ester

Nicotine Nicotine, l-methyl-2-(3-piridyl)pirrolidine (13.1.27), is an alkaloid that is isolated from the plant Nicotiana (Nicotiana tabacum, Nicotiam rustica, and others) and can be synthesized in varions ways [33-36]. In particular, it is proposed to proceed from nicotinic acid ethyl ester, which is condensed with iV-methylpyrrolidone, giving l-methyl-2-nicotinoyl pyrrolidone-2 (13.1.23). Acidic hydrolysis of this compound leads to an opening of the pyrrolidine ring giving the intermediate (13.1.24), which under the reaction conditions is decarboxylated to the /-aminoketone (13.1.25). The carbonyl group is reduced to an alcohol and the resnlting prodnct (13.1.26) undergoes dehydration to nicotine (13.1.27). 

Ethyl-nicotinic acid ethyl ester [Et2Nic] C10H14NO2 180.22... 

Ethyl-nicotinic acid ethyl ester Ethylsulfate 1141-12 l-Butyl-3-methylpyridinium bromide... 

CAS 614-18-6 EINECS/ELINCS 210-370-7 Synonyms 3-Carbethoxypyridine 3-(Ethoxycarbonyl) pyridine Ethyl 3-pyridinecarboxylate Nicotinic acid, ethyl ester Picolinic acid ethyl ester 3-Pyridinecarboxylic acid, ethyl ester p-Pyridinecarboxylic acid, ethyl ester Empiricai C8H9NO2... 

Nicotinic acid, ethyl ester. See Ethyl nicotinate... 

Figure 28 Electrokinetic separation of the niacin derivatives in the presence of SDS. Conditions applied voltage, 15 kV sample injection, injected by raising the positive end of the capillary about 4 cm higher than the other end capillary, a polyimide-coated fused-silica (70 cm X 50 xm i.d.) micellar solution, 0.15 M SDS in 0.02 M borate-0.01 M KOH (pH 9.1) detection wavelength, 210 nm. 1, Isonicotinic acid hydrazide 2, Nam 3, pyri-dine-3-methanol 4, 6-AN 5, MNA 6, pyridine-3-aldehyde 7, pyridine 8, 3-acetylpyri-dine 9, thionicotinamide 10, NiA 11, pyridine-3-sulfonic acid 12, P-picoline 13, nicotinic acid ethyl ester. (From Ref. 71.)...

Picolinic acid, 3,6-dichloro-. See Clopyralid Picolinic acid ethyl ester. See Ethyl nicotinate P-Picolyl alcohol. See Pyridine-3-methanol PicoPure . See Hydrogen peroxide Picramic acid. See 2-Amino-4,6-dinitrophenol Picramic acid, sodium salt. See Sodium picramate... 

Pyridine-3-carboxylic acid ethyl ester (ethyl nicotinate)... 

Method 1. Reflux a mixture of pure nicotinic acid (Section V,22), 84 g. (105 ml.) of absolute ethanol and 90 g. (50 ml.) of concentrated sulphuric acid in a flask for 4 hours on a steam bath. Cool the solution and pour it slowly and with stirring on to 200 g. of crushed ice. Add sufficient ammonia solution to render the resulting solution strongly alkaline generally, some ester separates as an oil but most of it remains dissolved in the alkaline solution. Extract the solution with five 25 ml. portions of ether, dry the combined ethereal extracts with anhydrous magnesium sulphate, remove the ether and distil under reduced pressure. The ethyl nicotinate passes over at 117-118°/ 6 mm. the yield is 34 g. The b.p. under normal pressure is 222-224°. 

The reaction products are 2,4-dimethyl-3-acetylpyridine (11) and ethyl ester of 2,4-dimethyl-3-nicotinic acid (12). 

Hydroxycynnclidine (14.1.17) is synthesized from the methyl ester of wo-nicotinic acid, which is reacted with the ethyl ester of bromoacetic acid to give the piridinium salt (14.1.14). This is rednced by hydrogen nsing a platinnm catalyst, giving 1-carbethoxymethyl-... 

Furo[3,4-r]pyridine derivatives are generated from the reaction of 2,3-dihalopropenyl ketones with the ethyl ester of / -aminocrotonic acid. Initial reaction products are substituted nicotinic acids which can be partially converted into the furopyridines under harsh vacuum distillation conditions (Scheme 12) <2005CHE1009>. 

Hotchkiss, S.A.M., Hewitt, P. Caldwell, J. (1992) Percutaneous absorption of nicotinic acid, phenol, benzoic acid and triclopyr butoxy ethyl ester through rat and human skin in vitro further validation of an in vitro model by comparison with in vivo data. Food chem. Toxicol., 30,891-899... 

Pyka and Sliwiok separated six esters of nicotinic acids methyl nicotinate, ethyl nicotinate, isopropyl nicotinate, butyl nicotinate, hexyl nicotinate, and benzyl nicotinate by adsorption HPLC on a LiChrospher Si 60 column. The mixtures containing benzene and methanol in volume proportions (O-i-lO, 1h-9, 2h-8, 3h-7, 4-1-6, and 5-1-5) were used as the mobile phases. The (min) values of esters investigated have been correlated with the dipole moments (/imph) of the mobile phases apphed, with numerical values of one topological index from among those based on the distance matrix (A, W, °7J, B) or the... 

Equations 28 and 29 can also be used to predict the Jr values of the esters of nicotinic acid, whose measurement points have not been taken into consideration in the equation. A test was performed on Eqs. 28 and 29 to determine how well they predict r values of points not included in the training set. Three values were removed from the training sets (Eqs. 28 and 29). Isopropyl nicotinate (separated in benzene methanol, 5 5, voFvol) and ethyl nicotinate (separated in benzene methanol, 4 6, and 0 10, voFvol) from Eqs. 28 and 29 were removed. This subset of two parametric equations was recalculated as ... 

Esterification. Carboxylic acids are converted into their ethyl esters when heated with an excess of the reagent. Even hindered acids such as 2,4,6-trimethylbenzoic acid are esterified. An acid catalyst usually is not necessary and may be deleterious however, esterification of nicotinic acid and of hippuric acid was accomplished with p-toluenesulfonic acid in dimethylformamide. 

These nicotinic acid intermediates were also converted to their corresponding ethyl esters by reaction with ethyl alcohol in the presence of sulfuric acid. Surprisingly, the alkyl amides had some pre- and postemergent herbicidal activity with bleaching symptomology. The activity was quite weak, less than 50% weed control was observed at 2 lb/acre. The esters, on the other hand, were almost devoid of herbicidal activity. 

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