Phosphoric Acid → HCID 15670957, compound

HRID 2371429Notes

Reaction equation

HRID 2371429 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.P(=O)(O)(O)O.[CH2:18]=[CH:19][C:20](=[CH2:22])[CH3:21]>C1C=CC=CC=1>[CH3:21][C:20]1([CH3:22])[O:1][C:2]2[C:3](=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 6557IsopreneHCID 1770652,6-Dihydroxyquinoline

Product 1

HCID 15670957HCID 15670957, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

6-hydroxyquinoline-2-one (481 mg) and orthophosphoric acid (0.55 ml) were dissolved in 5 ml of benzene, and then a solution of 0.55 ml of isoprene in 5 ml of benzene was added thereto with stirring. The resulting mixture was heated under reflux for 30 minutes. The reaction liquid was poured into ice-cold water and extracted with ethyl acetate. The extracted liquor was washed with water, dehydrated by addition of anhydrous sodium sulfate and filtered. The solvent in the filtrate was distilled away under reduced pressure, and the resulting residue was recrystallized from ethanol to give 567 mg of pale yellow needle-like crystals.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customThe reaction liquid
  4. additionwas poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe extracted liquor was washed with water
  7. additiondehydrated by addition of anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationThe solvent in the filtrate was distilled away under reduced pressure
  10. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1261fff3e7a94db39b21ae182da64c05
Source dataset
uspto-grants-1992_03
Patent number
US05093339

Reaction notes

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