Diisobutylaluminum hydride → [2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

HRID 451224Notes

Reaction equation

HRID 451224 reaction equation
[CH:1]1([C:4]2[C:13]([C:14](OC)=[O:15])=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[C:13]([CH2:14][OH:15])=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 9901664Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

Product 1

HCID 9817555[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

To 50 g of methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate added toluene (250 ml) and stirred for 15 minutes at 25° C. Cooled the reaction mixture to 0° C. Added 300 ml of DIBAL H (25% solution in toluene) to the reaction mixture slowly in 45 minutes at the same temperature. Stirred the reaction mixture for 1 hr at 0° C. Quenched the reaction mixture with HCl (110 ml) solution at 10° C. and stirred for 15 minutes. Raised the temperature to 25° C. and stirred for 30 minutes. Separated the both aqueous and organic layers. Extracted the aqueous layer with toluene (400 ml). Adjusted the pH of the reaction mixture with 10% sodium bicarbonate solution (200 ml). Washed the organic layer with saturated sodium chloride solution (200 ml). Distilled off the solvent completely to obtain a solid. Added cyclohexane (50 ml) to the solid and distilled it. To the residue added cyclohexane (150 ml) and stir for 30 minutes at 45° C. Cooled the reaction mixture to 25° C. and stirred for 1 hr. at the same temperature. Filtered the cake, washed with cyclohexane (50 ml) and then dried to get the title compound.

Workup

  1. temperatureCooled the reaction mixture to 0° C
  2. stirringStirred the reaction mixture for 1 hr at 0° C
  3. customQuenched the reaction mixture with HCl (110 ml) solution at 10° C.
  4. stirringstirred for 15 minutes
  5. temperatureRaised the temperature to 25° C.
  6. stirringstirred for 30 minutes
  7. customSeparated the both aqueous and organic layers
  8. extractionExtracted the aqueous layer with toluene (400 ml)
  9. washWashed the organic layer with saturated sodium chloride solution (200 ml)
  10. distillationDistilled off the solvent completely
  11. customto obtain a solid
  12. distillationAdded cyclohexane (50 ml) to the solid and distilled it
  13. additionTo the residue added cyclohexane (150 ml)
  14. stirringstir for 30 minutes at 45° C
  15. temperatureCooled the reaction mixture to 25° C.
  16. stirringstirred for 1 hr
  17. filtrationFiltered the cake
  18. washwashed with cyclohexane (50 ml)
  19. customdried

Sources & evidence

ORD record
ord-8c3dc20979cb40548ed4525d1e440c73
Source dataset
uspto-grants-2013_07
Patent number
US08487105B2

Reaction notes

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