Thionyl Chloride → HCID 68828999, compound

HRID 1986414Notes

Reaction equation

HRID 1986414 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16]O)=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S(Cl)(Cl)=O.[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][N:32]1[C:28](=[O:38])[C:29]3[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31]1=[O:33])=[C:5]2[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24194345Phthalimide potassium saltHCID 68829046HCID 68829046, compound

Product 1

HCID 68828999HCID 68828999, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (6-chloro-2-isobutyl-4-phenylquinolin-3-yl)methanol (0.70 g, 2.15 mmol) in toluene (15 ml) was added thionyl chloride (0.31 ml, 4.3 mmol), and the mixture was heated under reflux for 1 hr. The reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (50 ml). The organic layer was washed with saturated brine (20 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was dissolved in N,N-dimethylformamide (10 ml). Thereto was added potassium phthalimide (0.6 g, 3.2 mmol) and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (50 ml)-water (50 ml). The aqueous layer was extracted with ethyl acetate (50 ml) and the extract and the organic layer were combined. The mixture was washed twice with water (50 ml) and then saturated brine (50 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give 2-[(6-chloro-2-isobutyl-4-phenylquinolin-3-yl)methyl]-1-H-isoindole-1,3(2H)-dione (0.55 g, yield 57%) as an orange oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (50 ml)
  4. washThe organic layer was washed with saturated brine (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in N,N-dimethylformamide (10 ml)
  8. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium hydrogen carbonate (50 ml)-water (50 ml)
  9. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
  10. extractionthe extract
  11. washThe mixture was washed twice with water (50 ml)
  12. dry with materialsaturated brine (50 ml), and dried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3ced3aea99c455abe79daf817f4d305
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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