5-chloro-1H-indole-2,3-dione → 5-Chloro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

HRID 2102653ノート

反応式

HRID 2102653 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22]>O1CCCC1>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

参加物

4

反応物 2

HCID 872035-chloro-1H-indole-2,3-dioneHCID 178491912HCID 178491912、化合物

生成物 1

HCID 225609075-Chloro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-25 °C

実験手順

A solution of 4-methoxyphenyl magnesium bromide in tetrahydrofuran (0.5 M, 50 mL, 25 mmol) (Aldrich) was added dropwise to a suspension of 5-chloroisatin (1.82 g, 10 mmol) (Avocado) in tetrahydrofuran (20 mL) under argon with cooling in a −25° C. bath and magnetic stirring at such a rate that reaction temperature was kept below −10° C. (approximately 30 minutes). Cooling bath was then removed and mixture allowed to warm to room temperature. After stirring for an additional 1 hour, 15% aqueous ammonium chloride solution (50 mL) was added and mixture extracted with ethyl acetate (2×75 mL). Ethyl acetate layers were then washed with water (75 mL), brine (75 mL), combined, dried (MgSO4), filtered and concentrated. Residue was stirred in dichloromethane (100 mL) at room temperature for 30 minutes and filtered to give crude rac-5-chloro-3-hydroxy-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one as a white powder. (Yield 2.57 g, 88.7%).

後処理

  1. customthat reaction temperature
  2. customwas kept below −10° C.
  3. custom(approximately 30 minutes)
  4. temperatureCooling bath
  5. customwas then removed
  6. temperatureto warm to room temperature
  7. stirringAfter stirring for an additional 1 hour
  8. addition15% aqueous ammonium chloride solution (50 mL) was added
  9. extractionmixture extracted with ethyl acetate (2×75 mL)
  10. washEthyl acetate layers were then washed with water (75 mL), brine (75 mL)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. stirringResidue was stirred in dichloromethane (100 mL) at room temperature for 30 minutes
  15. filtrationfiltered

出典と根拠

ORDレコード
ord-91cda980f6434b6ea96b3b3d21a732a5
出典データセット
uspto-grants-2009_08
特許番号
US07576082B2

反応ノート

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