Reaction #1563909

Reaction equation

N-(6-iodobenzo[d][1,3]dioxol-5-yl)acetamide

NaOH

→

6-iodobenzo[d][1,3]dioxol-5-amine

Yield 98.5%

Solvents

ethanol

water

Conditions

Workup

1. 1
   Temperatureto reflux
2. 2
   TemperatureThe mixture was cooled
3. 3
   Otherthe solvent was removed under vacuum
4. 4
   OtherThe residue was partitioned between methylene chloride (100 mL) and water (100 mL)
5. 5
   WashThe organic layer was washed with water (2×100 mL)
6. 6
   Dryingdried (MgSO4)
7. 7
   Otherevaporated under vacuum

Procedure

A solution of N-(6-iodobenzo[d][1,3]dioxol-5-yl)acetamide (200 mg, 0.656 mmol) and NaOH (1.31 g, 32.8 mmol) in ethanol (26 mL) and water (6 mL) was heated to reflux with stirring for 4 h. The mixture was cooled and the solvent was removed under vacuum. The residue was partitioned between methylene chloride (100 mL) and water (100 mL). The organic layer was washed with water (2×100 mL), dried (MgSO4) and evaporated under vacuum to give 6-iodobenzo[d][1,3]dioxol-5-amine (170 mg, 98%) as orange solid. LCMS: 264 [M+1]+; 1H NMR (DMSO-d6) δ 4.88 (s, 2H), 5.87 (s, 2H), 6.47 (s, 1H), 7.07 (s, 1H).

Source