Nicotinoyl chloride

The present method is that described by Rinderknecht and Ma.3 4 It is equally applicable to a variety of other heterocyclic, aromatic, and aliphatic anhydrides.4,6 Nicotinic anhydride was first prepared by reaction of nicotinoyl chloride with sodium nicotinate,6,7 and more recently by reaction of potassium nico-tinate with oxalyl chloride in anhydrous benzene.2... 

CJH4N2 100-54-9) see Nicotinamide Nicotinyl alcohol nicotinoyl chloride... 

CSH4CINO 10400-19-8) see Etofibrate Hepronicate Inositol nicotinate Micinicate Niaprazine Niceritrol Nicoclonate Nicotafuryl Nifenazone Ronifibrate nicotinoyl chloride hydrochloride (C( H,Cl2NO 20260-53-1) see Nicofuranose nitric acid... 

Syntheses of naphthyridone derivatives follow the same procedures as those of quinolones, except that substituted 2-aminopyridines (Gould-Jacobs modification) or substituted nicotinic ester/nicotinoyl chloride are used instead of anilines or o-halobenzoic acid derivatives. Most of the recently introduced quinolone antibacterials possess bicyclic or chiral amino moieties at the C-7 position, which result in the formation of enantiomeric mixtures. In general, one of the enantiomers is the active isomer, therefore the stereospecific synthesis and enantiomeric purity of these amino moieties before proceeding to the final step of nucleophilic substitution at the C-7 position of quinolone is of prime importance. The enantiomeric purity of other quinolones such as ofloxacin (a racemic mixture) plays a major role in the improvement of the antibacterial efficacy and pharmacokinetics of these enan-... 

The amino group of 8-amino-l 1 //-pyrido [2,1 -b]quinazolin-l 1 -one was acylated with nicotinoyl chloride (89MI1). The nitro group of 2-nitro-6,7,8,9-tetrahydro-ri//-pyrido[2,l-6]quinazolin-ll-one (120, R = 2-N02) was reduced to an amino group which was acylated to give 2-acetamido and 2-benzamido derivatives [85IJC(B)336],... 

When nicotinic acid is heated for 8 hours at 180° with thionyl chloride, a low yield of 5-chloronicotiriic acid is obtained.182 The orientation observed in this case suggests an electrophilic attack, perhaps on a complexed nicotinic acid chloride molecule (which would thus behave somewhat like a pyridine A-oxide). If the reaction is carried out at 150° and the reaction time lengthened to 50 hours, a 30% yield of 5,6-dichloronicotinic acid is obtained.182 Both mechanistic pathways may be involved here. Isonicotinic acid reacts with thionyl chloride at 180-220°, presumably by, way of an electrophilic attack since 3-chloro-and 3,5-dichloroisonicotinic acid are formed.182 Nicotinoyl chloride (from nicotinic acid and thionyl chloride—probably in the complexed form) gives an 87% yield of 5-bromonicotinic acid on reaction with bromine for 10 hours at 150-1700.185... 

In order to improve cell and blood-brain-barrier permeability of the polar tetrahydropterins model studies were performed by applying the concepts of the Bodor system. 6-Mono- and 6,7-disubstituted 5,6,7,8-tetrahydropterins (172) have been acylated with nicotinoyl chloride at N-5 (173) followed by quaternization of the pyridine moiety by various alkyl and aralkyl halides (174), respectively (Scheme 27). Reduction of the pyridinium residue to its 1,4-dihydro stage afforded new types of potentially active conjugates (175) (Scheme 27) <90MI 718-07,91MI718-03). 

Another example of an unexpected acylation reaction is the action of excess nicotinoyl chlorides on enaminones leading to fused pyridopyrimidines or to spiro compounds57. 

The reaction apparently proceeds with both 3- and 4-nicotinoyl chlorides by an initial acylation of the jS-carbon of the enaminone. The reaction is followed by action of nucleophilic enaminone nitrogen on the 4-position of the pyridine ring to form spiro compounds or naphthyridones in moderate yield (equation 39). 

Acylation of Imines with Nicotinoyl Chloride (Route a)... 

Similarly, acylation of imine 22 with nicotinoyl chloride afforded enamide 27 when one mole of the acid chloride was used, whereas acylation with an excessive amount of the acid chloride yielded the already cyclized dihydroazaberbine (28) in good yield, which was also obtained from the enamide by acylation (67). Hydrolysis of 28 afforded the corresponding azaberbine (26) (Scheme 26) (6 7). 

Acylation of either 1-methylisoquinolines with an excessive amount of nicotinoyl chloride or the enamide with the same acid chloride yielded the... 

Nauclefine. In 1975 Sainsbury and Webb (122) and Hotellier et al. (71) reported the isolation and synthesis of nauclefine. Hotellier et al. (71) obtained nauclefine in 6% by treating harmalane with an excessive amount of nicotinoyl chloride. Alternatively, Sainsbury and Webb (122) carried out photocyclization of the enamide 201, prepared from harmalane and the above acid chloride, to obtain a mixture of two lactams, 29 and 202, in the ratio of 100 9, with 48% yield. The major product thus obtained was identical to parvine, whose name was first proposed by Sainsbury (122) but later changed to nauclefine (123) (Schemes 77 and 78). 

They utilized the reaction between indole Grignard reagents and either 3-acetyl-pyridine or nicotinoyl chloride to give the target structures 54 and 365, after the appropriate reduction. None of these compounds displayed antitumor activity anywhere comparable to that of ellipticine. 

First, CD polyrotaxanes were synthesized by us by polymer analogous reaction of the amino groups of the PI-ll/a-CD pseudopolyrotaxane with nicotinoyl chloride. A 25% conversion of the imino groups led to a permanent 67% coverage of... 

The formation of a trinicotinate was reported.2409 The best method of preparing this starch derivative involved reacting nicotinoyl chloride hydrochloride and starch in boiling pyridine.2410 Starch isonicotinates and 4-(sulfinylamino)benzoates were subsequently prepared. Starch isonicotinate was further cationized by treating it in nitromethane solution with methyl 2-(chloroacetyl)lactate or benzoylhydrazide A-chloroacetate and l-[2-(chloroacetoxy)propanoyl]-3-methylpyrazole.2411... 

Nicotinoyl chloride 1119 Oxalyl chloride (12.5 g) in dry benzene (25 ml) is dropped into a suspension of dry, powdered potassium nicotinate (16.1 g) in dry benzene (75 ml), stirred and cooled in an ice-bath. After 15-20 minutes further stirring, the unmelted ice is removed from the bath, which is allowed to come to room temperature and then heated to the b.p. within 30 min. After cooling, the mixture is filtered from KC1, freed from solvent at water-... 

Molina and co-workers employed iminophosphoranes derived from a-azido-ketones in their one-step syntheses of oxazole alkaloids (Scheme 1.75). Reaction of 4-methoxyphenacyl azide with nicotinoyl chloride in the presence of triphenylphos-phine gave O-methylhalfordinol 280 directly in 56% yield. Similarly, reaction of 4-methoxyphenacyl azide with 3,4-dimethoxycinnamoyl chloride gave annuloline 281 in comparable yield after chromatographic purification. The authors proposed initial formation of an iminophosphorane, which was acylated with elimination of triphenylphosphine oxide to afford an imidoyl chloride, which then cychzed to the oxazole. 

The a-keto ester XI-6S was synthesized in good yields by treating 3-nicotinoyl chloride with a Wittig reagent. Treatment of the oxime of... 

Acylation of 9% -inositol or its 1,2-acetal derivatives mth chloroacetyl diloride, chlorobutanoyl chloride or nicotinoyl chloride gives tetra-acetate or hcxa-acetate derivatives with antiischemic activity. ... 

Addition of iV-nucleophiles converts nitriles into amidoximes, amidines, amidrazones, etc., which are valuable intermediates, especially for the preparation of heterocycles. For example amidoxime prepared from p-hydroxybenzo[ C]nitrile and hydroxylamine, reacted with nicotinoyl chloride to give 3,5-disubstituted l,2,4-[3- C]oxadiazole the... 

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