Ammonium Chloride → HCID 67606149, compound

Participants

Reaction Steps

1.2 g (2.04 mmol) of {4-[3-(4-cyano phenoxy)-5-(3-nitro benzyloxy)benzoyl amino]cyclohexyl}carbamic acid tert-butyl ester, dissolved in 10 ml of THF, 0.455 g (8.16 mmol) of iron powder and 0.436 g (8.16 mmol) of NH4Cl solution (5 ml water) were mixed. The resulting reaction mixture was refluxed overnight. After completion of reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. 100 ml water was added to the concentrated mixture and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with water followed by saturated brine, dried over anhydrous sodium sulphate and concentrated to afford crude compound which was purified by column chromatography using hexane-ethylacetate (10:2) to afford 0.75 g of the required product. 1H NMR (DMSO-d6): δ 1.25 (4H, m), 1.4 (9H, s), 1.8 (4H, m), 3.2 (1H, m), 3.7 (1H, m), 5.0 (2H, s), 5.15 (2H, s), 6.5 (2H, m), 6.62 (1H, s), 6.78 (1H, d), 6.94 (1H, s), 7.0 (1H, t), 7.12 (3H, m), 7.4 (1H, s), 7.82 (2H, d), 8.26 (1H, d).

Provenance & Evidence