8-Hydroxyquinoline → HCID 21783328、化合物

HRID 1802054ノート

反応式

HRID 1802054 の反応式
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][CH:5]=1)([O-:3])=[O:2].I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=1)([O-:3])=[O:2]

参加物

9

反応物 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 1458133-Nitropyrrole

生成物 1

HCID 21783328HCID 21783328、化合物収率 91.2%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-nitropyrrole (270 mg, 2.41 mmol), iodobenzene (0.267 mL, 2.39 mmol), 8-hydroxyquinoline (60 mg, 0.41 mmol) and K2CO3 (600 mg, 4.34 mmol) in DMSO (3 mL) was degassed with argon before being charged with CuI (45 mg, 0.23 mmol). The mixture in a sealed tube was heated at 130 C for 20 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 3-nitro-1-phenyl-1H-pyrrole (410 mg).

後処理

  1. customwas degassed with argon
  2. temperatureThe mixture in a sealed tube was heated at 130 C for 20 h
  3. customThe organic phase was separated
  4. washwashed with 1N HCl
  5. dry with materialwith 5% NaHCO3, dried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6f41b02c433d4ae2a4729e649a0494ab
出典データセット
uspto-grants-2013_01
特許番号
US08349860B2

反応ノート

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