Ethyl Acetate → 4-Acetamino-2-cyanobiphenyl

HRID 976557Notes

Reaction equation

HRID 976557 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:2].[C:18](OCC)(=[O:20])[CH3:19]>[Pd]>[NH:9]([C:7]1[CH:6]=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]([C:1]#[N:2])[CH:8]=1)[C:18]([CH3:19])=[O:20]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 214689572-Cyano-4-nitrobiphenyl

Product 1

HCID 214688684-Acetamino-2-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-Cyano-4-nitrobiphenyl (0.067 moles, 15.0 g.) was dissolved in 100 ml ethyl acetate/100 ml ethanol and hydrogenated at 40 psi over 3.0 g of 10% palladium on carbon. The catalyst was removed by filtering though colire. The solvents were removed in vacuo. The residue was dissolved in 175 ml of methylene chloride. Acetic anhydride (15 ml) was added. The reaction was stirred at room temperature for 30 minutes and poured over ice. The organic layer was dried, concentrated, and then purified by HPLC over silica gel eluted with a gradient of 0-10% ethyl acetate in chloroform. (HS)

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering though colire
  3. customThe solvents were removed in vacuo
  4. dissolutionThe residue was dissolved in 175 ml of methylene chloride
  5. additionAcetic anhydride (15 ml) was added
  6. additionpoured over ice
  7. customThe organic layer was dried
  8. concentrationconcentrated
  9. custompurified by HPLC over silica gel
  10. washeluted with a gradient of 0-10% ethyl acetate in chloroform

Sources & evidence

ORD record
ord-8afa62c68ce54f0b8b0dab9ecdf88b31
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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