Calcium Chloride → HCID 18428678, compound

Participants

Reaction Steps

A mixture of the nitro compound of Example 21 (400 mg, 1.18 mmol), iron powder (591 mg, 10.6 mmol) and calcium chloride (65 mg, 0.59 mmol) in 85% aqueous ethanol (15 mL) was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and filtered through Celite®, washing thoroughly with ethanol and then ethyl acetate. The solvent was removed in vacuo and the residue was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (95:5:0.5)] to give the desired aniline compound (299 mg, 82%) as a beige solid; δH(CDCI3, 300 MHz) 2.20 (6 H, s), 3.27 (2 H, s), 3.63 (2 H, brs), 6.60 (1 H, dd), 6.80 (1 H, d), 6.87 (1 H, d), 6.90 (2 H, d), 7.50 (2 H, d); MS m/z (TS+) 310 (MH+).

Provenance & Evidence