5-Nitro-2,3-dihydro-1,4-benzodioxine → 2,3-Dihydro-1,4-benzodioxin-5-amine

HRID 1487199Notes

Reaction equation

HRID 1487199 reaction equation
[N+:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[O:9]1[CH2:10][CH2:11][O:12][C:13]2[C:4]([NH2:1])=[CH:5][CH:6]=[CH:7][C:8]1=2

Participants

4

Reactant 1

HCID 122313185-Nitro-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 117883872,3-Dihydro-1,4-benzodioxin-5-amineYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5-nitro-2,3-dihydrobenzo[b][1,4]dioxine (8 g, 0.044 mol) and palladium on carbon (10%, 2 g) in methanol (250 mL) was stirred vigorously under an atmosphere of hydrogen overnight at room temperature. The mixture was filtered through a pad of Celite and then concentrated to give the crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 9/1) to afford the product 2,3-dihydrobenzo[b][1,4]dioxin-5-amine (6.5 g, yield 97%). 1H NMR (400 MHz, CDCl3) δ ppm 6.61-6.65 (t, 1H, J=8.0 Hz), 6.30-6.33 (dt, 2H, J=1.2 Hz, 2.4 Hz), 4.22-4.27 (m, 4H), 3.75 (s, 2H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customto give the crude product, which
  4. customwas purified by silica gel column chromatography (petroleum ether/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-000205da7a27472e998c44a04789d47b
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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