Carbon Dioxide → 8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one

HRID 969456Notes

Reaction equation

HRID 969456 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:23])[CH2:21]Cl)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]2[CH2:21][O:23]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 22499245HCID 22499245, compound

Product 1

HCID 138976418-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 20 g (61 mmol) 8-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one in 160 mL DMF is added dropwise at 0° C. to 35 mL of a 4 molar sodium hydroxide solution and then stirred for 2 hours at this temperature. The reaction mixture is combined with 1.5 L ice water, buffered by the addition of dry ice and extracted with ethyl acetate. The organic phases are dried with sodium sulphate, the solvent is distilled off and the residue is chromatographed over aluminium oxide (dichloromethane/ethyl acetate gradient). The fractions containing the product are evaporated down to 60 mL and then combined with petroleum ether, during which time a solid is precipitated, which is suction filtered and dried.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phases are dried with sodium sulphate
  3. distillationthe solvent is distilled off
  4. customthe residue is chromatographed over aluminium oxide (dichloromethane/ethyl acetate gradient)
  5. additionThe fractions containing the product
  6. customare evaporated down to 60 mL
  7. customis precipitated
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-0e33c9a5286c4fa9b0b9b3d0c8e2781f
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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