Dimethyl Sulfoxide → HCID 22493527, compound

HRID 2269233Notes

Reaction equation

HRID 2269233 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([CH2:24][OH:25])[CH:20]=[C:19]2[CH3:26])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CCCCCC.O>[CH:11]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([CH:24]=[O:25])[CH:20]=[C:19]2[CH3:26])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22493573HCID 22493573, compound

Product 1

HCID 22493527HCID 22493527, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

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. stirringby stirring for 15 minutes
  2. stirringstirring for 5 minutes
  3. stirringstirred for one hour
  4. extractionthe resulting solution was extracted with dichloromethane
  5. washThe organic layer was successively washed with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue so obtained

Sources & evidence

ORD record
ord-ee297bc7377e4fbbb1399a8fed3f1545
Source dataset
uspto-grants-2001_12
Patent number
US06329402B1

Reaction notes

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