Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines
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Abstract
The preparation of difluoropyridines by the Schiemann reaction was investigated. 2-Amino-6-fluoropyridine (IIIa), necessary for the synthesis of 2,6-difluoropyridine (IVa) by the Schiemann reaction, was conveniently prepared by the Curtius degradation of 6-fluoropicolinic hydrazide (IIa) and by the Hofmann reaction on 6-fluoropicolinamide (IId). Since an α-fluorine on a pyridine nucleus is preferentially replaced by hydrazine when it is either adjacent to or opposite a carbomethoxy group, the hydrazides necessary for the synthesis of 3-amino-2- and 6-fluoropyridine could not be prepared. These amines were prepared from the appropriate 2-fluoropyridinecarboxamide by the Hofmann reaction. The preparation of difluoropyridines was successful with two of the aminofluoropyridines and led to the following new compounds: 2,3-difluoro(IVb) and 2,6-difluoropyridine (IVa).
| Publication type | Article |
|---|---|
| Publication Subtype | Journal Article |
| Title | Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines |
| Series title | Journal of Organic Chemistry |
| DOI | 10.1021/jo01058a050 |
| Volume | 27 |
| Issue | 11 |
| Year Published | 1962 |
| Language | English |
| Publisher | American Chemical Society |
| Description | 4 p. |
| First page | 3965 |
| Last page | 3968 |
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