Hydrochloric Acid → HCID 70126961, compound

HRID 1376793Notes

Reaction equation

HRID 1376793 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.Cl.[O-:23][C:24]#[N:25].[Na+]>>[NH:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:24]([NH2:25])=[O:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 517096Sodium CyanateHCID 53909416HCID 53909416, compound

Product 1

HCID 70126961HCID 70126961, compoundYield 50%

Procedure

A mixture of 5-amino-3-[(7-azaindol-3-yl)methylene]-2-oxindole (2.773 g, 10 mmol) in ice water (20 ml) are added 5N HCl (2 ml, 10 mmol) under stirring. Then the mixture was heated to 70°14 80° C., sodium cyanate (0.715 g, 11 mmol) was added portionwise and the stirring was continued for further 4 h at this temperature. After cooling the raw product was extracted with CHCl3, the organic layer washed to neutrality with saline solution, dried and evaporated in vacuo. The residue was chromatographed on silica gel using CHCl3 --MeOH mixtures as eluant to give pure title compound in about 50% yield.

Workup

  1. additionwas added portionwise
  2. extractionwas extracted with CHCl3
  3. washthe organic layer washed
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d4009328c50849ddabf0862092f66fb6
Source dataset
uspto-grants-1997_09
Patent number
US05663346

Reaction notes

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