Water → Indirubin-3'-monoxime

HRID 2170830Notes

Reaction equation

HRID 2170830 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][C:8]([OH:10])=[C:7]([C:11]3[C:19](=O)[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=3)[C:5]=2[CH:6]=1.[Cl-].[OH:22][NH3+:23].O>N1C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][C:8]([OH:10])=[C:7]([C:11]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19]=3[N:23]=[O:22])[C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 101772H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-HCID 21645Hydroxylamine HCl

Product 1

HCID 3707Indirubin-3'-monoximeYield 90.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Indirubin (0.64 g, 2.4 mmol) was dissolved in anhydrous pyridine (25 mL), and hydroxylammonium chloride (1.67 g, 24 mmol) was added to the solution. The reaction liquid was heated and refluxed for 2.5 hours and then cooled to room temperature. The reaction liquid was poured into water (100 mL), and the precipitated crude crystals were collected by suction filtration. The resulting crude crystals were recrystallized from methanol/water to give red needle-shaped crystals of indirubin-3′-oxime (0.60 g, 89%).

Workup

  1. customThe reaction liquid
  2. temperaturewas heated
  3. temperaturerefluxed for 2.5 hours
  4. customThe reaction liquid
  5. customthe precipitated crude crystals
  6. filtrationwere collected by suction filtration
  7. customThe resulting crude crystals were recrystallized from methanol/water

Sources & evidence

ORD record
ord-39632d1f5b3d4e7081ce75a444af585b
Source dataset
uspto-grants-2015_06
Patent number
US09051306B2

Reaction notes

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