Water → 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-

HRID 2170829Notes

Reaction equation

HRID 2170829 reaction equation
CC([O:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=O.[NH:14]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=O)[C:15]1=[O:16].C(=O)([O-])[O-].[Na+].[Na+].O>CO>[CH:21]1[CH:22]=[CH:23][C:24]2[NH:14][C:15]([OH:16])=[C:17]([C:6]3[C:5](=[O:4])[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:7]=3)[C:19]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7054IsatinHCID 10340Sodium CarbonateHCID 11841Indoxyl acetate

Product 1

HCID 101772H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-Yield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Argon gas was blown into a suspension of indoxyl acetate (1.75 g, 10 mmol) and isatin (1.47 g, 10 mmol) in anhydrous methanol (20 mL) for 5 minutes. Sodium carbonate (2.12 g, 20 mmol) was added to the reaction liquid and stirred at room temperature for 18 hours. The reaction liquid was then poured into water (1 L). The precipitated crude crystals were collected by suction filtration. The resulting crude crystals were recrystallized from 1,4-dioxane/hexane to give purple needle-shaped crystals of indirubin (1.81 g, 69%).

Workup

  1. customThe reaction liquid
  2. customThe precipitated crude crystals
  3. filtrationwere collected by suction filtration
  4. customThe resulting crude crystals were recrystallized from 1,4-dioxane/hexane

Sources & evidence

ORD record
ord-30cea05770bc462e902cffa231059acd
Source dataset
uspto-grants-2015_06
Patent number
US09051306B2

Reaction notes

Loading…