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

HRID 968280ノート

反応式

HRID 968280 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418647HCID 178418647、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
23 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a2f448999d40424ab97dd6965d58f4b6
出典データセット
uspto-grants-2005_10
特許番号
US06958347B2

反応ノート

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