Methanol → 2-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

HRID 11638노트

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HRID 11638 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.ClC[C:11]1[CH:19]=[CH:18][CH:17]=[C:13]([C:14](N)=[O:15])[C:12]=1[C:20]([NH2:22])=[O:21].[CH3:23]O>[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:3]=1)[CH2:23][N:22]1[C:20](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:11]=2)[C:14]1=[O:15]

참가 물질

5

반응물 3

HCID 887MethanolHCID 46844-ChlorophenolHCID 21973291Chloromethylphthalamide

생성물 1

HCID 219732982-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

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온도
90 °C

실험 절차

To 4-chlorophenol (2.0 g, 15.5 mmol) and chloromethylphthalamide (2.62 g, 13.4 mmol) was added zinc chloride (3 mL, 0.5 M in tetrahydrofuran, 1.5 mmol). The reaction was stirred at 90° C. for 48 hours. After cooling the reaction was diluted with methanol (15 mL) and brought to reflux. After 30 minutes the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. Methanol (50 mL) was again added and the reaction brought to reflux. After 3 hours the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. The crude product was purified via chromatography on silica gel to give the title compound (3.86 g).

후처리

  1. temperatureAfter cooling the reaction
  2. temperatureto reflux
  3. filtrationAfter 30 minutes the hot suspension was filtered through a medium glass frit
  4. concentrationconcentrated to an off-white solid
  5. additionMethanol (50 mL) was again added
  6. temperatureto reflux
  7. filtrationAfter 3 hours the hot suspension was filtered through a medium glass frit
  8. concentrationconcentrated to an off-white solid
  9. customThe crude product was purified via chromatography on silica gel

출처 및 근거

ORD 기록
ord-e670c84d8b25493984d67a7d7e5b877b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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