2,2-Dimethyl-6-nitro-2H,4H-1,3-benzodioxin-4-one → 6-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

HRID 551887

Reaction equation

HRID 551887 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]([CH3:14])([CH3:13])[O:10][C:11](=[O:12])[C:6]=2[CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]([CH3:13])([CH3:14])[O:10][C:11](=[O:12])[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 597024542,2-Dimethyl-6-nitro-2H,4H-1,3-benzodioxin-4-one

Product 1

HCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-oneYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-nitro-2,2-dimethyl-4H-1,3-benzodioxin-4-one (4.1 g) in EtOH (30 mL) was added Pd/C (1.947 g) under nitrogen atmosphere. Hydrogenation was performed for 12 hrs at rt using 10 bars of H2. The reaction mixture was filtered through X bed of celite, washed with EtOH and THF. The filtrates were concentrated under vacuum to give the title compound as a pale yellow solid (3.5 g, 98%). 1H NMR (CDCl3) δ 7.71 (d, J=8.7 Hz, 1H), 7.15 (d, J=2.6 Hz, 1H), 6.83 (dd, J=8.7 Hz, 2.6 Hz, 1H), 3.44 (brs, 2H), 2.63 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through X bed of celite
  2. washwashed with EtOH and THF
  3. concentrationThe filtrates were concentrated under vacuum

Sources & evidence

ORD record
ord-e299140d23f141d8b2969bd939542929
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Linked notes

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