4-Chloroaniline → HCID 63623460, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloroaniline (0.26 g, 2.0 mmol) was dissolved in methanol (25 ml). Then 3-oxetanone (0.22 g, 3 mmol) and zinc chloride (1.09 g, 8.0 mmol) were added and the reaction mixture was cooled with an ice bath. After adding sodium cyanoborohydride (0.377 g, 6.0 mmol) the mixture was allowed to stir at 40° C. for 5 hours. After cooling, the reaction mixture was poured onto ammonium chloride/ice and extracted with ethyl acetate (3 times 20 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=95:5) to yield a light yellow liquid (108 mg, 29%); 1H-NMR (CDCl3): 4.14 b, 1H(NH); 4.55 m, 3H(CHO, CHN); 5.00 t, 2H(CHO), 6.43 d, 2H (aryl-H) and 7.15 d, 2H (aryl-H).

Provenance & Evidence