Ethanol → 3-Iodo-4-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

In a 3-neck 250 mL round-bottomed flask equipped with a stir bar, condenser and N2 lines was placed iron powder (3.50 g, 62.7 mmol), ammonium chloride (4.88 g, 91.3 mmol), ethanol (72 mL) and water (23 mL). The mixture was heated to 85° C. and then 2-iodo-1-methoxy-4-nitro-benzene (5.0 g, 17.9 mmol) was added portion wise over a period of about 2 minutes. The mixture was allowed to stir at 85° C. for 2 hours and then filtered through celite. The celite was washed with EtOH (100 mL) and the filtrate was concentrated. To the concentrated material was added water (100 mL) and ethyl acetate (150 mL). The organic portion was removed and the aqueous portion was re-extracted with ethyl acetate (150 mL). The organic portions were combined, washed with brine (150 mL), dried (MgSO4) and concentrated. The crude material was purified by column chromatography utilizing 50% EtOAc/hexanes as the eluent to produce 3.92 g of 3-iodo-4-methoxy-phenylamine (I-45, X═I, Y═H, Z═NH2, R1═CH3) as a brown semi-solid in 88% yield. MS (ESI+): 250.1 (M+1)

Provenance & Evidence