Iodine → 5-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

HRID 552302

反応式

HRID 552302 の反応式
[Mg].II.Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12].[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[C:17]2=[O:24].[NH4+].[Cl-]>CCOCC.O>[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[C:17]2([OH:24])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12]

参加物

8

反応物 5

HCID 807IodineHCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

生成物 1

HCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
20 °C

実験手順

40 g (1.65 mol) magnesium shavings were overlaid with 100 ml ether, and after the addition of a small amount of iodine, they were carefully heated until the reaction kicked off. 203 ml (1.65 mol) bromanisole, dissolved in 450 ml ether, were dropped in to the boiling solution so slowly that the reaction continually proceeded at a low boil. Subsequently, with slight cooling to 20° C., 75 g (0.41 mol) 5-chlorisatin in 750 ml water-free tetrahydrofurane were added in by drops. After this, everything was stirred for 30 minutes more at room temperature. The reaction solution was poured into an aqueous NH4Cl solution while being stirred. This aqueous phase was extracted a number of times with ethyl acetate and the combined aqueous phases were washed with water four times, dried and concentrated in a vacuum. The residue obtained was crystallised from isopropanol, wherein 106 g of the intermediate product resulted.

後処理

  1. temperaturewere carefully heated until the reaction
  2. additionwere dropped in to the boiling solution so slowly that the reaction
  3. stirringwhile being stirred
  4. extractionThis aqueous phase was extracted a number of times with ethyl acetate
  5. washthe combined aqueous phases were washed with water four times
  6. customdried
  7. concentrationconcentrated in a vacuum
  8. customThe residue obtained
  9. customwas crystallised from isopropanol, wherein 106 g of the intermediate product
  10. customresulted

出典と根拠

ORDレコード
ord-88e0a1f133ca41278c6589fdf10551a2
出典データセット
uspto-grants-2011_05
特許番号
US07951807B2

関連ノート

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