7-Methoxy-2-(2-methyl-1,3-dioxolan-2-yl)-4-nitro-1-benzofuran → 7-Methoxy-2-(2-methyl-1,3-dioxolan-2-yl)-1-benzofuran-4-amine

HRID 1441918Notes

Reaction equation

HRID 1441918 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)=[CH:8][C:7]=2[C:6]([N+:18]([O-])=O)=[CH:5][CH:4]=1>C(O)C.[Pd]>[NH2:18][C:6]1[C:7]2[CH:8]=[C:9]([C:12]3([CH3:17])[O:13][CH2:14][CH2:15][O:16]3)[O:10][C:11]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 1

HCID 574581737-Methoxy-2-(2-methyl-1,3-dioxolan-2-yl)-4-nitro-1-benzofuran

Product 1

HCID 685415577-Methoxy-2-(2-methyl-1,3-dioxolan-2-yl)-1-benzofuran-4-amineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 10% Pd on activated carbon (200 mg) in ethanol (100 mL), under N2 protection, was added 7-methoxy-2-(2-methyl-(1,3-dioxolan-2-yl))-4-nitrobenzofuran (6.50 g, 23 mmol). The reaction mixture was degassed under vacuum three times. The reaction mixture was stirred vigorously while hydrogen gas was allowed to flow over the reaction mixture. After 4 h the reaction was complete by TLC (5:1 hex:EA). The reaction mixture was filtered through a pad of celite and the celite was rinsed with additional ethanol. The solvent was removed in-vacuo to obtain 5.1 g (88% yield) of the title compound as a yellow oil.

Workup

  1. customThe reaction mixture was degassed under vacuum three times
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe celite was rinsed with additional ethanol
  4. customThe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-dc9f42dc47b846c18c0e218fafc1e90c
Source dataset
uspto-grants-2010_02
Patent number
US07655802B2

Reaction notes

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