OS(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:21])[CH2:15][CH:16](OC)OC)[CH:10]=[CH:11][CH:12]=1>O>[F:6][C:7]1[CH:8]=[C:9]2[C:10]([CH:16]=[CH:15][C:14](=[O:21])[NH:13]2)=[CH:11][CH:12]=1A solution of 70% H2SO4 was made up by adding chilled H2SO4 (35 ml) to chilled water (15 ml) ensuring the temp remained between 10-20° C. Finely ground N-(3-fluorophenyl)-3,3-bis(methyloxy)propanamide (6.17 g, 27.2 mmol) was then added cautiously to this solution keeping the vessel in ice. This was stirred for 1 hour and then ice water (70 ml) was added. This was then diluted further with water (230 ml). The mixture was stirred for a further 30 mins. The precipitate was filtered off and dried in a vacuum oven overnight to give the desired product (3.67 g, 83%). This material contained approximately 10% of the isomeric 5-fluoro-2(1H)-quinolinone.
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