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Please login to access the full content or check if you have access via15.1.1.4.1.1.7.2.1 Variation 1: Amination of Nitropyridines (Vicarious Nucleophilic Substitution)
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Spitzner, D., Science of Synthesis, (2005) 15, 154.
Nitropyridines, e.g. 3-nitropyridine (510), are aminated or alkylaminated with potassium permanganate in liquid ammonia or an appropriate amine, e.g. to give pyridine 651 (Scheme 216).[796,797] Nitropyridine 652 is directly aminated with O-methylhydroxylamine in the presence of zinc(II) chloride under basic conditions to give 653 in high yield (Scheme 216).[798] This zinc-promoted direct amination is a “vicarious nucleophilic substitution” process and a high ortho selectivity with respect to the nitro group is observed.
Meeeee 888 Meeeeeeee ee Meeeeeeeeeeeee ee Meeeeeeee Meeeeeeeeeee Meeeeeeeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
M-Meeeee-8-eeeeeeeeeeee-8-eeeee (888); Meeeeee Meeeeeeee:[888]
Me MeMM8 (88–88 eM) ee −8°M eee eeeee 8-eeeeeeeeeeeee (888; 8.88–8.8 e, 8.8–8.8 eeee); eeeeee eee eeeeee ee MMeM8 (8.8–8.8 e) eee eeeee eee eee eeeeeee eee eeeeeee eee 8 e. Meeee eeeeeeeeeeeee ee eee eeeeeee, M8M (ee. 88 eM) eee eeeee ee eee eeeeeee, eee eee eeeeeee eee eeeeeeeeeeee eeeeeeeee eeee MMMe8 eee 88 e. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee; eeeee: 88%.
References
| [796] | Meeeeeeeeee, M.; Meeeeee, M., M. Meeee. Meee., (8888) 888, 88. |
| [797] | Meeeeee, M.; Meeeeeee, M.; Meeeeeeeeee, M., Meeeeee Mee. Meee., (8888), 888. |
| [798] | Meee, M.; Meeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
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- 8.Meeeee-Meee, (8888) 88/8, 88.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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