16554-45-3

2-Methoxy-6-nitroaniline is useful for preparing pyrimidine derivatives as FGFR4 inhibitors.

Step 1: Synthesis of 2-methoxy-6-nitroaniline; A mixture of 2-amino-3-nitrophenol (11.66 g, 76 mmol) and potassium carbonate (K2CO3, 12.55 g, 91 mmol) was stirred in N,N-dimethylformamide (DMF, 100 mL) for 1 hour. Subsequently, a solution of iodomethane (5.68 mL, 91 mmol) in DMF (10 mL) was added dropwise and the reaction mixture was continued to be stirred for 14 hours. After completion of the reaction, the reaction mixture was diluted with distilled water (H2O) and extracted with ethyl acetate (EtOAc, 2 × 100 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give a dark solid. The crude product was purified by recrystallization from hexane to give 2-amino-3-nitroanisole as an orange solid (11.6 g, 91% yield). Liquid chromatography-mass spectrometry (LCMS, ES+) showed m/z 169.0 ([M + H]+).

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