Hydrochloric Acid → HCID 57436587, compound

Participants

Reaction Steps

2-(3-(N,N-Dimethylamino)methylphenyl)-4-nitroanisole (200 mg, 0.70 mmol) was dissolved in EtOH/H2O (5 mL:2.5 mL). concentrated HCl (40 uL) was added, followed by iron powder (314 mg). The reaction mixture was refluxed for 1 h, allowed to cool to room temperature, and diluted with EtOH (10 mL). The slurry was filtered and the filtrate evaporated. The resultant oil was taken up in 1 M NaOH (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic phases were dried (Na2SO4) and evaporated to afford 3-[3-(N,N-dimethylamino)methylphenyl]-4-methoxyaniline as a brown oil (102 mg, 0.40 mmol, 57%)

Provenance & Evidence