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

HRID 968280노트

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HRID 968280 반응식
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]

참가 물질

6

반응물 2

HCID 11776TriphenylphosphineHCID 22288547N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide

생성물 1

HCID 222885445-ethyl-9-nitro-5H-phenanthridin-6-one

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418647HCID 178418647, 화합물촉매HCID 6342Acetonitrile용매

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온도
23 °C

실험 절차

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.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe mixture was filtered through a plug of celite
  4. washthe filter cake was washed with ethyl acetate (100 ml) and diethyl ether (100 ml)
  5. washThe combined filtrates were washed with saturated sodium chloride (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationwere concentrated
  8. customThe residue was purified by flash column chromatography (150 ml diethyl ether followed by 150 ml of ethyl acetate)

출처 및 근거

ORD 기록
ord-a2f448999d40424ab97dd6965d58f4b6
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958347B2

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