Phosphoric Acid → HCID 15670956, compound

HRID 2371428Notes

Reaction equation

HRID 2371428 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][CH:20]=[CH2:21]>C1C=CC=CC=1>[CH3:18][CH:19]1[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)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 78451,3-ButadieneHCID 1770652,6-Dihydroxyquinoline

Product 1

HCID 15670956HCID 15670956, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
80 °C

Procedure

6-hydroxyquinoline-2-one (481 mg) and orthophosphoric acid (0.55 ml) were dissolved in 5 ml of benzene, and thereto was added dropwise with stirring 297 mg of butadiene dissolved in 5 ml of benzene. The resulting mixture was heated under reflux at 80° C. for 12 hours. The reaction liquid was poured into ice-cold water and extracted with 100 ml of ethyl acetate. The extracted liquor was washed with water and the ethyl acetate solution was dehydrated by addition of anhydrous sodium sulfate and filtered. The solvent in the filtrate was distilled away under reduced pressure. The resulting residue was recrystallized from ethanol to give 224 mg of white needle-like crystals.

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting mixture was heated
  3. customThe reaction liquid
  4. additionwas poured into ice-cold water
  5. extractionextracted with 100 ml of ethyl acetate
  6. washThe extracted liquor was washed with water
  7. additionthe ethyl acetate solution was dehydrated 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-27577c7e37654c75b963be671b0e5eea
Source dataset
uspto-grants-1992_03
Patent number
US05093339

Reaction notes

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