C([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([Cl:12])=[CH:7][C:6]=1[NH:13][CH:14]1[CH2:16][CH2:15]1)C.[Li+].[OH-].CO>C1COCC1>[Cl:12][C:8]1[C:9]([F:11])=[CH:10][C:5]([C:4]([OH:17])=[O:3])=[C:6]([NH:13][CH:14]2[CH2:15][CH2:16]2)[CH:7]=1A solution of 4-chloro-2-cyclopropylamino-5-fluoro-benzoic acid ethyl ester (Example B-3, 4.10 g, 15.9 mmol) in THF (100 mL) was reacted with an aqueous solution of 1.0 N LiOH (45 mL, 45 mmol) and methanol (40 mL) and allowed to stir overnight. The mixture was then concentrated to one-third volume and acidified with 1.0 N HCl. The mixture was extracted with ethyl acetate. the organic layers combined, dried with sodium sulfate, and concentrated to provide 3.0 g of the title compound as an oil.
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