3-Iodo-4-methoxybenzenamine

Into a 250-mL round-bottom flask was placed 2-iodo-l -methoxy-4-nitrobenzene (6 g, 21 , 50 mmol, 1.00 equiv), Fe (3.61 g, 3.00 equiv), NHNHTo 2-iodo-1-methoxy-4-nitrobenzene (485 mg, 1.74 mmol) suspended in methanol (6 mL) a solution of NHIntermediate step 4 toward 3-iodo-4-methoxy-aniline [00230] Dithionite (3.85 g, 22.15 mmol) as a slurry in water (20 mL) was added to mixture of 2-iodo-l-methoxy-4-nitro-benzene (1.03 g, 3.69 mmol) in MeOH (50 mL). The mixture was stirred for 5 m and then diluted with a saturated aq solution of NaHCC>3 (100 mL). The mixture was concentrated to half its volume under reduced pressure. The aq phase was extracted with EtOAc (3X50 mL), and the combined organic phases were washed with brine, dried over MgSC^, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography on silica gel, eluting with mixtures of hexanes and EtOAc to provide the title compound as a solid (0.652 g, 71percent). 1H NMR (300 MHz, CDC1Compound 2209A (209 mg, 0.84 mmol) and compound 2209B (311 mg, 0.92 mmol) were dissolved in methylene chloride (5 mL) and pyridine (5 mL) was added. The reaction was stirred at room temperature overnight and then quenched with 1N HCl (50 mL). The aqueous layer was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to provide the desired product (350 mg). 1H NMR (400 MHz, CDCl3) delta 7.61 (d, 1H), 7.25 (m, 1H), 7.2 (m, 2H), 6.8 (d, 1H), 3.85 (s, 3H), 1.5 (s, 9H).

Molecular Weight:249.05
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:248.96506
Monoisotopic Mass:248.96506
Topological Polar Surface Area:35.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes