7-Methoxy-2-methyl-4-nitro-1-benzofuran → HCID 11095186, compound

HRID 1881364Notes

Reaction equation

HRID 1881364 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])=[CH:8][C:7]=2[C:6]([N+:13]([O-])=O)=[CH:5][CH:4]=1>CCO.[Pd]>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])=[CH:8][C:7]=2[C:6]([NH2:13])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 132019017-Methoxy-2-methyl-4-nitro-1-benzofuran

Product 1

HCID 11095186HCID 11095186, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Methoxy-2-methyl-4-nitro-benzofuran (1.24 g, 6.0 mmol) was hydrogenated using Pd/C (10%, dry, 700 mg) and H2 balloon in EtOH (30 mL) at r.t. for 2 h. The reaction mixture was filtered. Purification of the concentrated filtrate by column chromatography (EtOAc:Hexane=2.5:7.5) afforded 7-methoxy-2-methyl-benzofuran-4-ylamine as a brown oil (620 mg, 58%). 7-Methoxy-2-methyl-benzofuran-4-ylamine (620 mg, 3.5 mmol) was dissolved in CH2Cl2 (10 mL). TCDI (thiocarbodiimidazole, 686 mg, 3.9 mmol) was added to the solution and the reaction mixture was stirred at r.t. for 30 min. Silica gel was added to the reaction mixture and the solvent was removed under vacuum. Purification of the silica gel coated crude product by flash column chromatography (EtOAc:Hexane=2:8) afforded the title product as a pale yellow oil (630 mg, 82%).

Workup

  1. customat r.t.
  2. customfor 2 h
  3. filtrationThe reaction mixture was filtered
  4. customPurification of the concentrated filtrate by column chromatography (EtOAc:Hexane=2.5:7.5)

Sources & evidence

ORD record
ord-d942229692f94ac88491c0027abc6a1a
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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