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The formation of 6-chloro-2-cyclopropyl-4-trifluoromethylquinolin-5-ol from 3-amino-6-chloro-2-(3-cyclopropyl-1-hydroxy-1-trifluoromethylprop-2-ynyl) phenol, obtained in situ by deprotection of the corresponding tert-butyldimethylsilyl ether with TBAF, has been briefly mentioned in the literature as an undesired reaction, but no further experimental details (including the product yield) have been given for this reaction: (a) Markwalder, J. A.; Mutlib, D. D. C. A.; Cordova, B. C., Klabe, R. M.; Seitz, S. P. Bioorg. Med. Chem. Lett. 2001, 11, 619-622.
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Formation of 6-chloro-2-cyclopropyl-4-trifluoromethylquinoline in 81% yield by refluxing a solution of 2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1- trifluorobut-3-yn-2-ol in chlorobenzene for 6 h has also been reported: (b) Choudhury, A.; Pierce, M. E.; Confalone, P. N. Synth. Commun. 2001, 31, 3707-3714.
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Unidentified chromatographically immobile materials were formed as a result of decomposition
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24 (see the Supporting Information for details). It is worth noting that in this latter case the authors have indicated the structure of the mononitrated product as 5-methoxy-2-nitroacetophenone rather than 3-methoxy-2-nitroacetophenone. The reduction of 3-methoxy-2-nitroacetophenone to give 2-amino-3-methoxyacetophenone was carried out as described in ref 24.
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24 (see the Supporting Information for details). It is worth noting that in this latter case the authors have indicated the structure of the mononitrated product as 5-methoxy-2-nitroacetophenone rather than 3-methoxy-2-nitroacetophenone. The reduction of 3-methoxy-2-nitroacetophenone to give 2-amino-3-methoxyacetophenone was carried out as described in ref 24.
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