By Author Unknown
ISBN-10: 0080576311
ISBN-13: 9780080576312
ISBN-10: 0120206447
ISBN-13: 9780120206445
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Sample text
Aminations according to Class of Compounds A. PYRIDINES An enormous amount of work has been carried out on the amination of alkylpyridines, and the work has been well documented (420R91; 54CRV449; 62HC(14,3)1; 67MI1; 74MI1). This section will cover the more recently reported aminopyridines. The amination products of some alkylpyridines are listed in Table V. Arylpyridines can also be aminated. For example, 2-phenylpyridine was aminated in DMA with sodium amide to give 6-amino-2-phenylpyridine in 87:/, yield (72KGS1642).
When the same substrate is treated with sodium amide under pressure, surprisingly, the result is the normal amino product of the Chichibabin reaction. Specific examples are described below. When 4-tert-butylpyridine (79)was heated with a mixture of xylene and sodium amide under 350 psi nitrogen pressure, allowing the hydrogen gas to escape through a pressure relief valve as the reaction proceeded, a yield of 74% 2-amino-4-tert-butylpyridine (80) was obtained. On the other hand, at atmospheric pressure coupling took place to (81) (Scheme 3 1).
Atmospheric pressure amination produced 2-aminoquinoline (78) (40MI 1). E. AMINATION A N D DIMERIZATION Dimerization is well known to be a side reaction in the Chichibabin reaction (78RCR1042). In fact, dimerization can be the only product with certain alkylpyridines (79USP4177349; 8 1USP4267335). Under normal Chichibabin conditions, heating a heterogeneous mixture of sodium amide in a hydrocarbon at atmospheric pressure with a branched chain alkylpyridine leads to 30 CHARLES K. McGILL AND ANGELA RAPPA Q (79) \ [Sec.
Advances in Heterocycling Chemistry. Vol. 44 by Author Unknown
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