Picolinium chloride

A) Preparation of 1-Methyl-2-Picolinium Chloride 98 ml of cx-picoline is dissolved in 200 ml of methanol, cooled and 85 ml (at -68°C) of methyl chloride is added. The solution is charged to an autoclave, sealed and the nitrogen pressure of 300 psig is established. The mixture is heated at 120° to 130°C for 2 hours, cooled and opened. The resulting solution is then evaporated to dryness in vacuo, yielding a residue of 110 g. This residue is then dissolved in 50 ml of water and extracted with two 50 ml portions of ether. The aqueous phase is then diluted to 150 ml with water and an assay for ionic chloride is performed which indicates the presence of chloride ion equivalent to 721 mg/ml of 1-methyl-2-picolinium chloride. 

B) Preparation of 2-(Hydroxyiminomethyl)-1-Methyl Pyridinium Chloride An aqueous solution of 15 ml of 1-methyl-2-picolinium chloride having a concentration of 477 mg/ml Is covered with 50 ml of benzene in an atmosphere of nitrogen and cooled to below 10°C. An aqueous solution of sodium hydroxide is added dropwise and the mixture is stirred for 5 minutes and allowed to stratify. The aqueous phase Is then drawn off and the benzene solution is added slowly to a solution of 3 ml of nitrosyl chloride in 175 ml of benzene containing 0.5 ml of dimethyl formamide at about 10°C in an atmosphere of nitrogen with good agitation. The mixture is then stirred for 1.5 hours and then extracted with four... 

Figure 14. Modification of charge density on carbon atoms of benzylpicolyl-magnesium and a-picolinium chloride calculated from C-13 NMR.

Pesticides. The compound 2-picoline is a component of l-[(4 -amino-2/- f-propyl-5 -pyrimidinyl )methyl]-2-picolinium chloride hydrochloride, known as Amprolium, a broad-spectrum coccidiostat. A newer coccidiostat is 3,5-dichloro-4-hvdToxy-2,6-lnfidine and known... 

Kreutzberger and Abel36 showed that treatment of />-nitrobenzyl-a-picolinium chloride (7a) with j-triazine in pyridine gave an 8% yield of the cyclized indolizine (9), presumably via the resonance-stabilized intermediate 8 (see Scheme 3). 

Carbohydrate metabolism provides the main energy source in coccidia. Diets deficient in thiamin, riboflavin, or nicotinic acid—all cofactors in carbohydrate metabolism—result in suppression of parasitic infestation of chickens by E tenella and E acervulina. A thiamin analog, amprolium—1-[(4-amino-2-propyl-5-pyrimidinyl)-methyl]-2-picolinium chloride—has long been used as an effective anticoccidial agent in chickens and cattle with relatively low host toxicity. The antiparasitic activity of amprolium is reversible by thiamin and is recognized to involve inhibition of thiamin transport in the parasite. Unfortunately, amprolium has a rather narrow spectrum of antiparasitic activity it has poor activity against toxoplasmosis, a closely related parasitic infection. 

Two other nucleophilic substitution reactions of pyridine iV-oxides deserve mention and further study to determine the effects of substituents. Pyridine N-oxide, benzoyl chloride, and the piperidine enamine of cyclohexanone give a good yield of 2-(2 -pyridyl)cyclo-hexanone (155) (63%).360 When W-methoxy-4-picolinium methyl... 

SYNS 1 -[(4-AMINO-2-PROPYL-5-PYRIMIDINYL)-METHYL]-2-METHYLPYRIDINIUM CHLORIDE l-(4-AMINO-2-n-PROPYL-5-PYRIMIDINYLMETHYL)-2-PICOLINIUM CHLORIDE CORID... 

Myristyl gamma-picolinium chloride 2 0.0195-0.169% w/v Depo-Provera (Pharmacia-Upjohn) 0.169% w/v... 

Methylprednisolone acetate Depo-Medrol (Pfizer) 3.5 to 7.0 drug 40 polyethylene glycol 3350 29 sodium chloride 8.7 Myristyl-gamma-picolinium chloride (preservative) 0.195 205-208"" / 2.56 intramuscular, intrasyn- ovial, intralesional... 

Atnino-2-propyl-5-pyrimidinyl)methyl]-2-picolinium chloride. 1- 4-Amino-2-propyl-5-pyrimidinyl)methyl)-2-picolinium chloride 1-((4-Amino-2-propyl-5-pyrimidinyl)methyl)-2-methylpyridinium chlorid Amprol, Veterinary Amprolio Amprolium Amprovine Corid EINECS 204-458-4 Pancoxin 2-Picolinium, 1-((4-amino-2-propyl-6-pyrimidinyljmethyl)-, chloride Pyridinium, 1-((4-amino-2-propyl-5-pyrimidinyl)methyl)-2-methyl-, chloride. Coccidiostat in veterinary medicine. Also used as an antiparasitic in cattle. Soluble in H2O, MeOH, EtOH, DMF, insoluble in i-PrOH, BuOH, dioxane, Me2CO, EtOAc, CH3CN, isooctane pH 2.6-3.0. 

Noninterfering methylcellulose, mystristyl-gamma-picolinium chloride, polyethylene glycol 4000, thimerosal... 

Methyl-l,5-diaminopentane, 413 Methylene chloride, 17, 182, 265, 291 2-Methyleneglutaric dinitrile, 392 Methyl ethyl ketone, 260, 454 Methyl isobutyl ketone, 525 Methyl mercaptan, 240 Methyl methacrylate, 29, 254 a-Methylnadic anhydride, 452 4-(a-Methylnadimido)-benzoic acid, 452 2-Methyl-5-nitroaniline, 454 2-Methylpentamethylenediamine, 392, 393, 399, 409 A -Methyl-4-picolinium hexafluorophosphate, 157 Methylpiperidine, 399 4-Methyl-pyrazolo[3.4-b]quinoline, 37... 

Angell and Moynihan have used the ideas of the quasilattice model of Gibbs and DiMarzio for the glassy state to define a characteristic temperature for transport phenomena. They and Easteal have applied this approach in the low-temperature region of inorganic melts as well as to ZnClg and its solutions with pyridinium chloride, a- and )ff-picolinium hydrochloride, and quinolinium hydrochloride. 

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