4-Nitro-2H-1,3-benzodioxole → 1,3-Benzodioxol-4-amine

HRID 1487220Notes

Reaction equation

HRID 1487220 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Ni]>[O:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([NH2:1])[C:12]=2[O:11][CH2:10]1

Participants

4

Reactant 1

HCID 125140994-Nitro-2H-1,3-benzodioxole

Product 1

HCID 103131651,3-Benzodioxol-4-amineYield 63.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-nitrobenzo[d][1,3]dioxole (2.0 g, 12 mmol) in ethanol (80 mL) was added Raney Ni (ca. 0.5 g). The mixture was stirred under an atmosphere of hydrogen for 4 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel chromatography (dichloromethane) to afford the product benzo[d][1,3]dioxol-4-amine (1.04 g, yield 63%). 1H NMR (400 MHz, CDCl3) δ ppm 6.64-6.68 (t, 1H, J=8.0 Hz), 6.29-6.35 (dt, 2H, J=0.8 Hz, 6.4 Hz), 5.90 (s, 2H), 3.52 (br, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-7e6ee8235e8d42d698f63a822fe77177
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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