1000802-34-5

N-(6-Iodobenzo[d][1,3]dioxol-5-yl)acetamide (200 mg, 0.656 mmol) was used as a raw material, which was dissolved with NaOH (1.31 g, 32.8 mmol) in a solvent mixture of ethanol (26 mL) and water (6 mL). The reaction mixture was heated to reflux under stirring and kept for 4 hours. Upon completion of the reaction, the mixture was cooled and the solvent was evaporated under reduced pressure. The residue was extracted by partitioning with dichloromethane (100 mL) and water (100 mL). The organic layer was separated and washed with distilled water (2 x 100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford 6-iodobenzo[d][1,3]dioxol-5-amine (170 mg, 98% yield) as an orange solid. The product was analyzed by LC-MS showing [M+1]+ m/z 264; 1H NMR (DMSO-d6) δ 4.88 (s, 2H), 5.87 (s, 2H), 6.47 (s, 1H), 7.07 (s, 1H).

[1] Patent: US2008/234314, 2008, A1. Location in patent: Page/Page column 59
[2] Patent: US2010/184801, 2010, A1
[3] Patent: US2016/317508, 2016, A1. Location in patent: Paragraph 0181
[4] Patent: WO2008/47109, 2008, A1. Location in patent: Page/Page column 56
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3922 - 3943