Hydrogen Peroxide → HCID 14501164, compound

HRID 2107314Notes

Reaction equation

HRID 2107314 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:3][CH2:2]1.[OH-:19].[K+].OO>CO>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]([C:17]([NH2:18])=[O:19])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 14501163HCID 14501163, compound

Product 1

HCID 14501164HCID 14501164, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.8 g of 5-morpholino-8-quinolinecarbonitrile (Compound No. 13) 60 ml of methanol was added and the mixture was stirred at 0° C. with further addition of an aqueous solution of 0.47 g of potassium hydroxide and then 5 ml of 30% hydrogen peroxide aqueous solution. The mixture was heated at 40° to 50° C. for 16 hours with stirring. After evaporation of the solvent, saturated sodium chloride aqueous solution was added to the residue, which was extracted with chloroform, and the extract was dried over anhydrous sodium sulfate. Chloroform was evaporated, and the residue was refined by column chromatography on silica gel using chloroform as an eluent. The crystals thus obtained were recrystallized from ethanol to yield 0.48 g (yield: 56%) of 5-morpholino-8-quinolinecarboxamide (Compound No. 22).

Workup

  1. temperatureThe mixture was heated at 40° to 50° C. for 16 hours
  2. customAfter evaporation of the solvent, saturated sodium chloride aqueous solution
  3. additionwas added to the residue, which
  4. extractionwas extracted with chloroform
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. customChloroform was evaporated
  7. customThe crystals thus obtained
  8. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-d1fc28a4323145568fca10366fad8a32
Source dataset
uspto-grants-1990_06
Patent number
US04933447

Reaction notes

Loading…