[Cl:1][C:2]1[C:11]([C:12](OCC)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[F:17])[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>ClCCl>[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[F:17])[N:3]=1A solution of quinolinecarboxylate (obtained in Stage 83f; 1.8 g; 6.7 mmol) in dichloromethane (40 ml) under argon is treated dropwise with diisobutylaluminium hydride (1M in dichloromethane; 20 ml; 20 mmol) at ambient temperature maintained at 10° C. by an ice-cooled water bath. The reaction mixture is agitated for 1 hour at ambient temperature, then poured onto a solution of sodium and potassium tartrate at 20% (200 ml). The resulting mixture is agitated vigorously for 1 hour, then filtered on celite. The filtrate is extracted with dichloromethane (2×100 ml). The combined extracts are washed with water and with a saturated solution of sodium chloride, then dried over magnesium sulphate and concentrated. Purification of the residue by chromatography at medium pressure (SiO2, CH2Cl2/MeOH, 98/2) yields 450 mg of a white solid (m.p.: 176° C.).
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