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

HRID 11638

反応式

HRID 11638 の反応式
[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]

参加物

5

反応物 3

HCID 887MethanolHCID 46844-ChlorophenolHCID 21973291Chloromethylphthalamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e670c84d8b25493984d67a7d7e5b877b
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

関連ノート

読み込み中…