HCID 53945300, compound → HCID 178488921, compound

Participants

Reaction Steps

Cyclopropanecarboxylic acid (2-methoxy-6-nitro-phenyl)-amide (5013) (7.80 g, 33.1 mmol) and iron powder (7.60 g) were suspended in acetic acid (200 mL) for 25 min at reflux. The reaction was concentrated and redissolved in ethyl acetate, and washed with NaHCO3 (sat. aq) and NaCl (sat. aq). The combined washings were dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography with 2% MeOH/CH2Cl2 and recrystallization from diethyl ether/hexane (3:1), yielding white crystals of 2-(cyclopropyl)-4-methoxylbenzimidazole (5014) (4.90 g, 26.1 mmol, 79% yield). 1H-NMR (200 MHz, CD2Cl2:) δ 7.07 (cm, 2H), 6.65 (cm, 1H), 3.90 (s, 3H, OCH3), 2.17-2.03 (m, 1H), 1.22-0.96 (m, 4H).

Provenance & Evidence