Hexane → HCID 22493573, compound

HRID 1816309Notes

Reaction equation

HRID 1816309 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14](OC)=[O:15])[CH:10]=[C:9]2[CH3:18])([CH3:3])[CH3:2].CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>O1CCCC1.O>[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([CH2:14][OH:15])[CH:10]=[C:9]2[CH3:18])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 22493561HCID 22493561, compound

Product 1

HCID 22493573HCID 22493573, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 8-isopropyl-4-methyl-2-quinolinecarboxylate was dissolved in 10 ml of tetrahydrofuran, followed by the dropwise addition of a 1M hexane solution of diisobutyl aluminum hydride at 0° C. under a nitrogen gas atmosphere. After stirring for 2 hours, saturated aqueous ammonium chloride was added to terminate the reaction. Water was added to the reaction mixture and the precipitate so formed was filtered. The filtrate was concentrated under reduced pressure, whereby 107 mg of 8-isopropyl-4-methylquinoline-2-methanol were obtained in the form of a colorless oil. Under a nitrogen gas stream, a solution of 210 μl of dimethyl sulfoxide in 0.5 ml of dichloromethane was added dropwise to a solution of 172 μl of oxalyl chloride in 1 ml of dichloromethane at −60° C. under a nitrogen gas stream, followed by stirring for 5 minutes. To the reaction mixture, a solution of 107 mg of 8-isopropyl-4-methyl-2-quinolinemethanol in 2 ml of dichloromethane was added dropwise, followed by stirring for 15 minutes, dropwise addition of 1 ml of triethylamine and stirring for 5 minutes. The reaction mixture was raised to room temperature and stirred for one hour. Water was added to the reaction mixture and the resulting solution was extracted with dichloromethane. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 3% ethyl acetate/n-hexane), whereby 87 mg of the title compound were obtained in the form of a pale yellow solid.

Workup

  1. customto terminate
  2. customthe reaction
  3. customthe precipitate so formed
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-53e6c417e11c4810b3b8bc2968c33cd8
Source dataset
uspto-grants-2005_04
Patent number
US06884808B2

Reaction notes

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