Triphenylphosphine → 9-chloro-5-ethyl-5H-phenanthridin-6-one

HRID 968285Notes

Reaction equation

HRID 968285 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:37]=[CH:36][C:24]([C:25]([N:27]([CH2:34][CH3:35])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])=[C:23](I)[CH:22]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(=O)([O-])[O-].[Ag+2]>[Cl:20][C:21]1[CH:37]=[C:36]2[C:24]([C:25](=[O:26])[N:27]([CH2:34][CH3:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=32)=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 222885394-chloro-N-ethyl-2-iodo-N-phenyl-benzamide

Product 1

HCID 222885519-chloro-5-ethyl-5H-phenanthridin-6-oneYield 63%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418647HCID 178418647, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

Palladium acetate (466 mg, 2.07 mol) was added to a suspension of silver carbonate (5.7 g, 20.7 mmol), triphenylphosphine (1.08 g, 4.15 mmol), and 4-chloro-N-ethyl-2-iodo-N-phenyl-benzamide I-14a (4.0 g, 10.4 mmol) in acetonitrile (52 ml). The reaction mixture was heated to reflux for 1 hour and cooled to 23° C. The mixture was filtered through a plug of celite and the filter cake was washed with ethyl acetate (50 ml) and diethyl ether (50 ml). The combined filtrates were washed with saturated sodium chloride (50 ml), dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by flash column chromatography (1% ethyl acetate in dichloromethane grading to 2% ethyl acetate in dichloromethane) to afford 9-Chloro-5-ethyl-5H-phenanthridin-6-one I-14b (1.68 g, 63%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe mixture was filtered through a plug of celite
  4. washthe filter cake was washed with ethyl acetate (50 ml) and diethyl ether (50 ml)
  5. washThe combined filtrates were washed with saturated sodium chloride (50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (1% ethyl acetate in dichloromethane grading to 2% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-03d06a9bc6054e8f8fda475171888702
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

Loading…