Sodium carbonate bicarbonate → 3-(7-Methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propanal

HRID 1847095Notes

Reaction equation

HRID 1847095 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11]([CH3:20])=[CH:10][C:9]1=[O:21].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O>Cl>[CH3:19][O:18][C:15]1[CH:16]=[C:17]2[C:12]([C:11]([CH3:20])=[CH:10][C:9](=[O:21])[N:8]2[CH2:7][CH2:6][CH:2]=[O:1])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 86624777Sodium carbonate bicarbonateHCID 867250161-[2-(1,3-Dioxolan-2-yl)ethyl]-7-methoxy-4-methylquinolin-2(1H)one

Product 1

HCID 867250173-(7-Methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propanalYield 74%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 1-[2-(1,3-dioxolan-2-yl)ethyl]-7-methoxy-4-methylquinolin-2(1H)one (30 ml) was added 4N hydrochloric acid (30 ml) and the mixture was stirred at room temperature for 2 hours. An aqueous solution of sodium carbonate/hydrogen carbonate was added to the reaction solution and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the obtained crude product was purified by thin layer chromatography (hexane/ethyl acetate) to yield 630 mg (74%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained crude product
  6. customwas purified by thin layer chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2e1ce78b3d804bf9a251f969555f06fc
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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