Nicotinyl chloride

Ethyl nicotiiiate may be prepared either by direct esterification of the acid with ethanol and sulphuric acid, followed by pouring into water and rendering ammouiocal or by interaction of the acid with thionyl chloride, followed by reaction of nicotinyl chloride hydrochloride with ethanol and subsequent neutralisation. 

Chloroseleno)nicotinyl chloride treated with primary aliphatic or aromatic amines gave 2-substituted 7-azabcnzisosclenazol-3(27/)-ones [51],... 

The synthesis of the glucosidic alkaloid buchananine has been reported (Scheme 5). The penultimate product (21), though crystalline, was shown by n.m.r. spectroscopy to be a mixture of a- and / -anomers, confirmed chemically by the last step, which led to a separable mixture of two tetra-acetates. This same mixture of acetates resulted when 1,2,3,4-tetra-O-acetyl-D-glucopyranose was esterified with nicotinyl chloride. It is concluded that buchananine is itself a mixture of a- and / -anomers (21), as a consequence of its ability to catalyse its own mutarotation.31... 

Reagents nicotinyl chloride, pyridine ii, 5M-HC1 (aq.) iii, Ac20, pyridine... 

Wenz and Keller also synthesized similar polyrotaxanes (5) (Figure 7) by threading a-CDs onto poly(iminomethylene) chains [20], Instead of attaching two bulky stoppers at the ends, however, they introduced blocking groups at arbitrary positions on the chain. More specifically, nonspecific reaction of the threaded polymer chain with nicotinyl chloride resulted in trapping of the CD rings located between the two nicotinamide units on the polymer backbone. 

Ester derivatives may be prepared using regular procedures such as heating the acid with an alcohol in the presence of hydrogen ions or starting with the nicotinyl chloride and an alcohol. The preparation of the amide derivative (nicotinamide) is described below. 

In the syntheses of 11-methoxynauclefine (433) (Scheme 3.75) and 11-methoxyrutaecarpine (440) (Scheme 3.76), Atta-ur-Rahman and Ghazala demonstrated how the pentacyclic yohimbine skeleton could be rapidly constructed from j8-carboline derivatives (125). Condensation of 391 with nicotinyl chloride (432) afforded the yohimbane 433 in addition to its seco-CD derivative 434 and pentacyclic analog 435. Thus, a one step synthesis of 11-methoxynauclefine (433) was achieved. 

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