Potassium Hydroxide → HCID 19036903, compound

HRID 264765Notes

Reaction equation

HRID 264765 reaction equation
[OH-:1].[K+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.O1CCO[CH2:17][CH:16]1[CH2:21][CH2:22]O>O>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:21]1[C:22]3[CH:6]=[CH:5][C:4]([C:12]4[CH:11]=[CH:10][CH:22]=[CH:21][C:16]=4[CH3:17])=[CH:17][C:16]=3[CH2:21][CH2:22][CH2:17][C:16]1=[C:7]2[C:8]([OH:13])=[O:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2365665-FluoroisatinHCID 23496530HCID 23496530, compound

Product 1

HCID 19036903HCID 19036903, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (790 mg, 12.0 mmol) was dissolved in 3 ml of water, and 400 mg (2.40 mmol) of 5-fluoroisatin was added thereto. To this was added 600 mg (2.40 mmol) of compound s obtained in Reference Example 19 which was dissolved in dioxane-ethanol (2 ml-4 ml). The mixture was heat-refluxed for 6 days. The solvent was distilled off, and the residue was dissolved in water and washed with ether. The aqueous layer was filtered through Celite, and acetic acid was added to the flitrate. The precipitated crystals were collected by filtration. These crystals were then dried under reduced pressure, and recrystallized from dimethylformamide-water to obtain 460 mg of the above-mentioned compound (yield 48%).

Workup

  1. customobtained in Reference Example 19 which
  2. temperatureThe mixture was heat-refluxed for 6 days
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in water
  5. washwashed with ether
  6. filtrationThe aqueous layer was filtered through Celite, and acetic acid
  7. additionwas added to the flitrate
  8. filtrationThe precipitated crystals were collected by filtration
  9. customThese crystals were then dried under reduced pressure
  10. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-ef5395167b814c01b887325808a1247e
Source dataset
uspto-grants-1997_07
Patent number
US05646283

Reaction notes

Loading…