Hydrochloric Acid → 3-Fluoro-4-(7-methoxyquinolin-4-yloxy)benzenamine

Participants

Reaction Conditions

Reaction Steps

To 4-(2-fluoro-4-nitrophenoxy)-7-methoxyquinoline (0.900 g, 2.9 mmol) in THF was added methanol (53 ml, 1297 mmol) and 1N HCl (8.6 ml, 8.6 mmol). The resulting mixture was cooled to 0° C. Iron (2.2 g, 40 mmol) was added, and the reaction was allowed to stir at RT for 3.5 hours. The reaction mixture was then diluted with MeOH, filtered through a pad of Celite, and concentrated in vacuo. The residue was then diluted with sat. NaHCO3 (aq) and CH2Cl2. The aqueous layer was separated and extracted three times with CH2Cl2. The combined organic extracts were dried over sodium sulfate and filtered through a pad of silica gel using 10% MeOH/CH2Cl2. The collected fractions were concentrated in vacuo and purified by silica gel chromatography (80 g column; 2% MeOH/CH2Cl2 for 10 minutes then 3.5% MeOH/CH2Cl2 for 10 minutes). Fractions containing pure product were concentrated to yield 3-fluoro-4-(7-methoxyquinolin-4-yloxy)benzenamine as a tan solid. Calcd for C16H13FN2O2: [M]+=284. Found: [M+H]+=285.

Provenance & Evidence