Dimethyl Sulfoxide → 2-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde

HRID 750263Notes

Reaction equation

HRID 750263 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[C:27]([CH2:28][OH:29])=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:36])[CH:24]=2)[C:19]1=[O:37])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C1COCC1.O>[CH2:11]([N:18]1[C:27]([CH:28]=[O:29])=[C:26]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:36])[CH:24]=2)[C:19]1=[O:37])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 230609532-benzyl-6-bromo-3-hydroxymethyl-4-phenyl-2H-isoquinolin-1-one

Product 1

HCID 230605422-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehydeYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under a nitrogen stream, to a solution of oxalyl chloride (0.54 ml) in THF (28 ml) was added dropwise a solution of DMSO (0.58 ml) in THF (5 ml) at −70° C. or below and the mixture was stirred for 10 min. A solution of 2-benzyl-6-bromo-3-hydroxymethyl-4-phenyl-2H-isoquinolin-1-one (1.30 g) in THF (7 ml) was added dropwise at −70° C. or below and the mixture was stirred at −60° C. to −50° C. for 1 hr. To the reaction mixture was added dropwise triethylamine (3.1 ml) at 50° C. or below and the mixture was allowed to warm to room temperature and stirred for 30 min. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethyl acetate-hexane to give the title compound (810 mg).

Workup

  1. stirringthe mixture was stirred at −60° C. to −50° C. for 1 hr
  2. stirringstirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-db44c299562f4bea80090e95d41dd899
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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