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

HRID 1374965

Reaktionsgleichung

Reaktionsgleichung von HRID 1374965
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]

Komponenten

8

Edukt 5

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

Produkt 1

HCID 210793831-(4-Isopropoxyphenyl)-1H-indole-2,3-dioneAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-762a474162cf4bfc98323d7edd6e7cb5
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166635B2

Verknüpfte Notizen

Wird geladen…