Hydrochloric Acid → 5-Ureido-3-(quinol-4-ylmethylene)-2-oxindole

HRID 356994Notes

Reaction equation

HRID 356994 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:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.Cl.[O-:24][C:25]#[N:26].[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:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1)[C:25]([NH2:26])=[O:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 517096Sodium CyanateHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

Product 1

HCID 676150015-Ureido-3-(quinol-4-ylmethylene)-2-oxindoleYield 50%

Procedure

To a mixture of 5-amino-3-(quinol-4-ylmethylene)-2-oxindole (2.873 g, 10 mmol) in ice water (20 ml) was added 5N HCl (2 ml, 10 mmol) under stirring. Then the mixture was heated to 70°-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. temperatureThen the mixture was heated to 70°-80° C.
  2. temperatureAfter cooling
  3. extractionthe raw product was extracted with CHCl3
  4. washthe organic layer washed
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b4425b770a6b4a36966e0c6e93a0ff61
Source dataset
uspto-grants-1998_11
Patent number
US05840745

Reaction notes

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