Pyrrolidine → 6-Nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole

Participants

Reaction Steps

A solution of 2-methyl-6-nitro-benzoxazole (30 mmol), dimethyl formamide dimethyl acetal (60 mmol) and pyrrolidine (60 mmol) in DMF (45 mL) is stirred at 100° C. for 16 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water and brine, dried (Na2SO4) and filtered. The filtrate is concentrated. The residue is washed with cooled EtOAc to afford 6-nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole as a solid. 1H NMR (300 MHz, CDCl3): δ 1.80-2.25 (broad, 4H), 3.10-3.80 (broad, 4H), 5.06 (d, H), 7.44 (d, H), 7.96 (d, H), 8.21 (m, 2H).

Provenance & Evidence