Hydrochloric Acid → 1-(4-Isopropoxyphenyl)-1H-indole-2,3-dione

HRID 1374965

反応式

HRID 1374965 の反応式
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[C:9]1=[O:18].[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([CH3:21])[CH3:20].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[C:9]2=[O:18])=[CH:25][CH:24]=1)([CH3:21])[CH3:20]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7054IsatinHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 36987264-Isopropoxybenzeneboronic acid

生成物 1

HCID 210793831-(4-Isopropoxyphenyl)-1H-indole-2,3-dione収率 39.7%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of triethylamine (28 g, 272 mmol) in CH2Cl2 (250 mL) was added to a mixture of 1H-indole-2,3-dione (10.0 g, 68 mmol), 4-isopropoxyphenylboronic acid (13.4 g, 75 mmol) and copper (II) acetate (5.0 g, 27 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The crude mixture was then treated with 1M HCl (3×350 mL), followed by aqueous saturated NaHCO3 solution (3×350 mL). The resulting organic faction was concentrated in vacuo and the residue was dissolved in CH2Cl2, dried over MgSO4, concentrated in vacuo, and re-suspended in CH2Cl2. The suspension was filtered and the filtrate was concentrated in vacuo. The crude product was recrystallized from a mixture of toluene/hexane (3:1), giving the desired product (7.6 g, 27 mmol).

後処理

  1. concentrationThe resulting organic faction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe suspension was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was recrystallized from a mixture of toluene/hexane (3:1)

出典と根拠

ORDレコード
ord-762a474162cf4bfc98323d7edd6e7cb5
出典データセット
uspto-grants-2007_01
特許番号
US07166635B2

関連ノート

読み込み中…