2- Methylnicotinic acid

Two year later, Pinel group used (S) proline and (S) pyroglutamic esters as chiral auxiliaries for the diastereoselective hydrogenation of 2 methylnicotinic acid with up to 35% de [50]. They tried to improve diastereoselectivity of these reactions, but no better result was obtained (Scheme 10.37). 

A simple procedure is described for the preparation of substituted 1,6-naphthyri-dinones in good yields from the dianions of 2-methylnicotinic acids (2002A80), 2-chloronicotinoyl chloride or 2,6-dichloro-5-fluoronicotinoyl chloride (2002T8543) and a-oxoketene <3,A-acetals (2003MI2). 

Trigonelline (1-methylnicotinic acid zwitterion) [535-83-1] M 137,1, m 218°(dec). Crystd (as monohydrate) from aqueous EtOH, then dried at 100°. 

Tinschert A, A Kiener, K Heinzmann, and A Tschech (1997) Isolation of new 6-methylnicotinic-acid-degrad-ing bacteria, one of which catalyses the regioselective hydroxylation of nicotinic acid at position Cj. Arch Microbiol 168 355-361. 

In general, niacin is widespread in foodstuffs (93,94). Cereals, seeds, meat, and fish are good food sources of niacin. The niacin content of coffee beans is primarily a product of the roasting process, which converts trigonelline (1-methylnicotinic acid) to nicotinic acid (95). 

In 1958, Ikekawa10 synthesized 2,7-naphthyridine and various substituted derivatives. His approach involved the reaction of 4-methylnicotinic acid with formaldehyde to afford the lactone 99 (R = H). The reaction of 99 with ammonia in methanol yields the amide (100) which, on oxidation with chromium trioxide, afforded 2,7-naphthyridin-l-one (101). This substance was converted into 2,7-naphthyridine (102, R = H) by consecutive treatment with phosphorus oxychloride, hydrazine, and copper sulfate. The 3-methyl derivative was similarly prepared starting with acetaldehyde. 

SYNS ARECAIDINE METHYL ESTER ARECOLINE BASE METHYL-1,2,5,6-TETRA-HYDRO-l-METHYL-NICOTINATE N-METHYL-A-TETRAHYDRONICOTIN-IC ACID METHYL ESTER N-METHYLTETRAHYDRO-PYRIDINE-P-CARBO-XYLIC ACID METHYL ESTER 1,2,5,6-TETRA-HYDRO-l-METHYLNICOTINIC ACID, METHYL ESTER... 

TETRAHYDRO-l-METHYLNICOTINIC ACID, METHYL ESTER see AQT750... 

Likewise, SOCL chlorinates 6-methylnicotinic acid (51) to trichloroni-cotinoyl chloride (52) (36JPRI88), whereas 4-methyl-nicotinic acid (53) is transformed by SOCL into the dichlorothio lactone 54 (44JAI456 ... 

C7H7BrO 2-bromo-4-methyl phenol 6627-55-0 25 00 1.5422 1 10642 C7H7N02 6-methylnicotinic acid 3222-47-7 37.08 1.2150 2... 

C7H8 5-ethylidene-1,3-cyclopentadiene 3839-50-7 380.68 32,548 2 10817 C7H8N202 2-amino-4-methylnicotinic acid 38076-82-3 525.65 46.354 2... 

An interesting transformation of various 4-methylnicotinic acids, in which the activated 4-methyl group enters into the reaction of the carboxyl group with thionyl chloride, leads to a l,3-dioxo-l,3-dihydrothienol 3,4-clpyridine74 [Eq. (22)1. 

Ricinine and ethionine were found to inhibit ricinine biosynthesis with shunting of radioactivity from [6- C]quinolinic acid through the pyridine nucleotide cycle into N-methylnicotinic acid (30) and N-methylnicotinamide (31) (c/. Scheme 6), and quinolinic acid consumption was reduced. 

Helv. Chim. Acta 2, 338 (1919) from 3-acetyl-1,4-dimethyl -1,2,5,6-tetrahydropyridine Prelog, Komzak, Ber. 74, 1705 (1941) from 7-methylnicotinic acid Rabe, Jantzen, Ber. 54, 925 (1921) from fl-ethy (pyridine KLoenigs, Hoffmann, Ber. 58, 194 (1925) from crotonaldehyde and ammonia Tschi-tschibabin, Oparina, Ber. 60, 1877 (1927). 

Tetrahydro-l-methylnicotinic acid, methyl ester 1,2,5,6-TetrahydrD-1-methyl-3-pyridinecarboxylic acid methyl ester. Used in veterinary medicine as an anthelmintic effective against Cestodes. Oil bp = 209" d n 1.0495 ngP= 1.4302 LDsO (mus sc) = 100 mg/kg. Boetmnger Ingelheim Vetmedica Inc. 

Nicotine.—Nicotine (33) is assembled in Nicotiana species from nicotinic acid (31) and N-methyl-A -pyrroline (32). Administration to Nicotiana plants of 5-fluoronicotinic acid and derivatives of (32) methylated at C-2 and C-3 has resulted in the formation in vivo of unnatural nicotine analogues.In contrast, 4-methylnicotinic acid has been found not to be transformed in vivo into 4-methylnicotine, presumably because this particular methyl group interferes sterically with the appropriate enzyme reactions involved in nicotine biosynthesis. ... 

TrigoneWne (1-methylpyridinium 3-carboxylate, N-methylnicotinic acid betaine). 

Trigonellln 1-methylnicotinic acid, a metabolite of nicotinic acid or nicotinamide found in many plants. It is both a hormone and a storage form of nicotinic acid. It is apparently not a niacin metabolite in animals, although it is found in the urine of coffee drinkers. Green coffee beans contain relatively large (> 500 mg/kg) amounts of X roasting the beans converts T. to nicotinic acid. Coffee is a significant dietary source of niacin (see Vitamins) in South and Central America. 

The use of cupric nitrate as a catalyst in these systems has also been described. The reaction usually proceeds to isocinchomeronic acid (X-5S, R = CO2 H), which is decarboxylated to nicotinic acid (X-S6) either in situ or in a subsequent operation. Under specific conditions of temperature and pressure, the reaction can be stopped at the 6-methylnicotinic acid (X-55, R = CHj) stage. It thus seems clear that under those conditions the 5-alkyl group is more prone to oxidative attack. The same nitric acid reaction system, with or without... 

Homonicotinic Acid i-Methylpyridine-B-carboxylic acid, i-methylnicotinic acid, y-picoUne-3-carboxyKc acid)... 

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