Thionyl Chloride → HCID 68832494, compound

HRID 1986417Notes

Reaction equation

HRID 1986417 reaction equation
[Br: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>[Br: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 68829518HCID 68829518, compound

Product 1

HCID 68832494HCID 68832494, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (6-bromo-2-isobutyl-4-phenylquinolin-3-yl)methanol (1.6 g, 4.2 mmol) in toluene (30 ml) was added thionyl chloride (0.61 ml, 8.4 mmol), and the mixture was heated under reflux for 30 min. The solvent was evaporated and the residue was dissolved in N,N-dimethylformamide (30 ml). Potassium phthalimide (1.2 g, 6.3 mmol) was added and the mixture was stirred at 55° C. for 1 hr. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml) and the aqueous layer was extracted with ethyl acetate (50 ml). The extract and the organic layer were combined and the mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml) and then saturated brine (50 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and toluene (20 ml)-ethyl acetate (10 ml) was added to the residue. Insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and crystallized from diisopropyl ether to give 2-[(6-bromo-2-isobutyl-4-phenylquinolin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione (1.7 g, yield 82%) as pale-yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in N,N-dimethylformamide (30 ml)
  5. customThe reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml)
  6. extractionthe aqueous layer was extracted with ethyl acetate (50 ml)
  7. extractionThe extract
  8. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  9. dry with materialsaturated brine (50 ml) and dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. additiontoluene (20 ml)-ethyl acetate (10 ml) was added to the residue
  12. filtrationInsoluble materials were filtered off
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography
  15. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-42d838951d3d425a8498c3761d338647
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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