Reaction #1563907

Reaction equation

NaHCO3

3,4-(Methylenedioxy)aniline

Ac2O

→

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

Yield 95.0%

Solvents

AcOH

Conditions

Workup

1. 1
   OtherAfter reaction
2. 2
   Filtrationfiltered
3. 3
   ExtractionThe filtrate was extracted with ethyl acetate

Procedure

To a solution of 3,4-(Methylenedioxy)aniline (8 g, 58.3 mmol) in AcOH (120 ml) was added Ac2O (48 mL). The mixture was stirred for overnight. After reaction, the mixture was poured into saturated NaHCO3 solution, and then filtered. The filtrate was extracted with ethyl acetate to give N-(benzo[d][1,3]dioxol-5-yl)acetamide (10 g, 95%). LCMS: 180[M+1]+; 1H NMR (DMSO-d6) δ 2.0 (s, 3H), 5.96 (s, 2H), 6.82 (d, 1H, J=8.1 Hz), 6.91 (d, 1H, J=2.1 Hz), 7.30 (d, 1H, J=1.8 Hz), 9.84 (s, 1H).

Source