Cesium carbonate → 1-(1,3-Dioxolan-2-ylmethyl)-7-methylquinolin-2(1h)-one

HRID 39686

Reaction equation

HRID 39686 reaction equation
Br[CH2:2][CH:3]1[O:7][CH2:6][CH2:5][O:4]1.[CH3:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CS(C)=O>[O:4]1[CH2:5][CH2:6][O:7][CH:3]1[CH2:2][N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([CH3:8])[CH:18]=2)[CH:13]=[CH:14][C:15]1=[O:19]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 776737-Methyl-2-quinoloneHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 593978351-(1,3-Dioxolan-2-ylmethyl)-7-methylquinolin-2(1h)-one

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To 6.3 mL of a dimethyl sulfoxide solution containing 1.1 g of 2-bromomethyl-1,3-dioxolane, 1.0 g of 7-methylquinolin-2(1H)-one and 3.1 g of cesium carbonate were added, and the mixture was stirred at 60 to 70° C. for 1 hour. The reaction mixture was added with ethyl acetate, water and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3] to obtain 0.60 g of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-methylquinolin-2(1H)-one.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3]

Sources & evidence

ORD record
ord-9041a22baa42428fbde1e34aa3e447f7
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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