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

HRID 1374965Notes

Reaction equation

HRID 1374965 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-762a474162cf4bfc98323d7edd6e7cb5
Source dataset
uspto-grants-2007_01
Patent number
US07166635B2

Reaction notes

Loading…