Acetic Acid → 2-(4-Pentylphenyl)quinoline-6-ol

HRID 1939115Notes

Reaction equation

HRID 1939115 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(O)(=O)C.Br>CCCCCC>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=3)[N:13]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 214668072-(4-Pentylphenyl)-6-methoxyquinoline

Product 1

HCID 214668092-(4-Pentylphenyl)quinoline-6-olYield 86.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

0.70 g (2.29 mM) of 2-(4-pentylphenyl)-6-methoxyquinoline, 4.6 ml of acetic acid and 4.3 ml of 47%-hydrobromic acid were placed in a 30 ml-round bottomed flask, followed by refluxing for 33 hours under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and dispersed in water. To the mixture, an appropriate amount of ethyl acetate was added, followed by stirring at room temperature. Under stirring, 1.5 g of sodium hydrogencarbonate was gradually added to the resultant mixture. The organic (ethyl acetate) layer was washed with water and dried with anhydrous sodium sulfate, followed by evaporation under reduced pressure to obtain a residue. To the residue, an appropriate amount of hexane was added, followed by filtration to obtain 0.58 g of 2-(4-pentylphenyl)-6-hydroxyquinoline (as a precipitated crystal) (Yield: 86.8%).

Workup

  1. temperatureby refluxing for 33 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. additiondispersed in water
  6. additionTo the mixture, an appropriate amount of ethyl acetate was added
  7. stirringby stirring at room temperature
  8. stirringUnder stirring
  9. addition1.5 g of sodium hydrogencarbonate was gradually added to the resultant mixture
  10. washThe organic (ethyl acetate) layer was washed with water
  11. dry with materialdried with anhydrous sodium sulfate
  12. customfollowed by evaporation under reduced pressure
  13. customto obtain a residue
  14. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-10ddaba197ce4922ad4e558a3dd033e7
Source dataset
uspto-grants-1997_12
Patent number
US05695684

Reaction notes

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