Triphenylphosphine → 5-ethyl-9-nitro-5H-phenanthridin-6-one
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23](=[O:34])[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=1I)[CH3:21]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:20]([N:22]1[C:23](=[O:34])[C:24]2[C:29](=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]1=2)[CH3:21]Participants
Conditions
- Temperature
- 23 °C
Procedure
Palladium acetate (826 mg, 3.68 mol) was added to a suspension of silver carbonate (10.1 g, 36.8 mmol), triphenylphosphine (1.93 g, 7.36 mmol), and N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide (7.29 g, 18.4 mmol) in acetonitrile (92 ml). The reaction mixture was heated to reflux for 30 minutes and cooled to 23° C. The mixture was filtered through a plug of celite, and the filter cake was washed with ethyl acetate (100 ml) and diethyl ether (100 ml). The combined filtrates were washed with saturated sodium chloride (100 ml), dried over anhydrous sodium sulfate, and were concentrated. The residue was purified by flash column chromatography (150 ml diethyl ether followed by 150 ml of ethyl acetate) afforded 5-ethyl-9-nitro-5H-phenanthridin-6-one I-1d (2.87 g, 58%) as a yellow solid.
Workup
- temperatureThe reaction mixture was heated
- temperatureto reflux for 30 minutes
- filtrationThe mixture was filtered through a plug of celite
- washthe filter cake was washed with ethyl acetate (100 ml) and diethyl ether (100 ml)
- washThe combined filtrates were washed with saturated sodium chloride (100 ml)
- dry with materialdried over anhydrous sodium sulfate
- concentrationwere concentrated
- customThe residue was purified by flash column chromatography (150 ml diethyl ether followed by 150 ml of ethyl acetate)
Sources & evidence
- ORD record
- ord-a2f448999d40424ab97dd6965d58f4b6
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06958347B2
Reaction notes
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