Potassium Carbonate → HCID 57067208, compound

HRID 562814Notes

Reaction equation

HRID 562814 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H: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.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H: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

4

Reactant 2

HCID 11430Potassium CarbonateHCID 54551328HCID 54551328, compound

Product 1

HCID 57067208HCID 57067208, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-Benzyloxy-5-((S)-2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one (0.55 g) is dissolved in acetone (20 mL). K2CO3 (0.58 g) is added and the reaction mixture is refluxed. The reaction is shown to be complete by TLC after 18 hours. The solvent is removed in vacuo and the residue is partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The product is triturated with diethyl ether, filtered and dried. TLC (silica, dichloromethane/methanol 25:1 Rf=0.45).

Workup

  1. temperaturethe reaction mixture is refluxed
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe product is triturated with diethyl ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-265f34259b56451a87145297820b1b2f
Source dataset
uspto-grants-2011_11
Patent number
US08067437B2

Reaction notes

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