Acetic Anhydride → HCID 17985729, compound

HRID 910099Notes

Reaction equation

HRID 910099 reaction equation
[N+:1]([C:4]1[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[C:7]([CH2:13][C:14]#[N:15])=[CH:6][CH:5]=1)([O-])=O.[C:16](OC(=O)C)(=[O:18])[CH3:17].O1CCCC1.[H][H]>[Pd].C(OCC)(=O)C>[C:14]([CH2:13][C:7]1[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[C:4]([NH:1][C:16](=[O:18])[CH3:17])=[CH:5][CH:6]=1)#[N:15]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 17985343HCID 17985343, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17985729HCID 17985729, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add (4-Nitrobenzofur-7-yl)acetonitrile (600 mg, 2.96 mmol), acetic anhydride (600 mg, 5.88 mmol), and 5% palladium on carbon (300 mg) to tetrahydrofuran (25 mL). Stir under 1 atmosphere of hydrogen for 45 minutes. Dilute with ethyl acetate, filter through a pad of Celite®, concentrate under reduced pressure, and chromatograph on flash silica using 75% ethyl acetate, 25% hexane to obtain the desired compound as an off-white solid (0.43 gm, 67%).

Workup

  1. filtrationfilter through a pad of Celite®
  2. concentrationconcentrate under reduced pressure, and chromatograph on flash silica using 75% ethyl acetate, 25% hexane

Sources & evidence

ORD record
ord-bf6f0036b40b4a51b5f3cd8e3d6d87d5
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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