Nitrosobenzene → 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

HRID 640816

反応式

HRID 640816 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=[O:8])([O-])=O.O=NC1C=CC=CC=1.CO.C(Cl)(Cl)Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=[O:8]

参加物

6

反応物 3

HCID 11473NitrosobenzeneHCID 21584188Chloroform methanolHCID 686984765-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

生成物 1

HCID 644240015-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one (2.0 g, 7.09 mmol) was dissolved in MeOH (600 mL). 10% Pd/C (0.20 g) was added to the flask and then placed under vacuum to remove any O2(g). The reaction mixture was kept under reduced pressure for ˜5 min and was then charged with H2(g) at atmospheric pressure. This evacuation/H2(g) fill procedure was repeated twice. The reaction mixture was stirred for 2 h at which point the starting material had been completely consumed. As the desired ketone product was prone to over-reduction to the alcohol, stopping the reaction immediately upon complete consumption of the starting material limited the amount over-reduction that occurred. The reaction mixture was filtered over celite and the filtrate was concentrated in vacuo resulting in a solid that contained the desired keto-aniline product plus ˜5% of the overreduced alcohol-aniline. Flash silica gel chromatography (5% MeOH/CHCl3) of the crude solid provided pure 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one in 72% (0.957 g, 3.80 mmol) yield.

後処理

  1. customto remove any O2(g)
  2. additionwas then charged with H2(g) at atmospheric pressure
  3. customhad been completely consumed
  4. customthe reaction
  5. customimmediately upon complete consumption of the starting material
  6. filtrationThe reaction mixture was filtered over celite
  7. concentrationthe filtrate was concentrated in vacuo
  8. customresulting in a solid

出典と根拠

ORDレコード
ord-39603ffa48544aa89dc76c98fbea4ec9
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

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