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

HRID 552302

반응식

HRID 552302 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-88e0a1f133ca41278c6589fdf10551a2
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951807B2

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