| 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 ??-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). |
| Genre: | Article |
| ProdID: | 70010794 |
| Citation Author: | Finger, G. C.; Starr, L. D.; Roe, A.; Link, W. J. |
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| Citation End Page: | 3968 |
| Citation Issue: | 11 |
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| Citation Language: | English |
| Citation Larger Work Title: | Journal of Organic Chemistry |
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| Citation Number Of Pages: | 4 |
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| Citation Publisher: | American Chemical Society |
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| Citation Search Results Text: | Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines; 1962; Article; Journal; Journal of Organic Chemistry; Finger, G. C.; Starr, L. D.; Roe, A.; Link, W. J. |
| Citation Start Page: | 3965 |
| Citation Volume: | 27 |
| Citation Year: | 1962 |
| Type: | citation/reference |
| Text: | Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines; 1962; Article; Journal; Journal of Organic Chemistry; Finger, G. C.; Starr, L. D.; Roe, A.; Link, W. J. |
| URL (THUMBNAIL): | http://pubs.er.usgs.gov/thumbnails/outside_thumb.jpg |
| URL (DIGITAL OBJECT IDENTIFIER): | http://dx.doi.org/10.1021/jo01058a050 |
| Date Other: | Mon, 1 Jan 1962 00:00 -0600 |
| Publisher: | American Chemical Society |
