Acetamidomalonic acid diethyl ester → HCID 54352082, compound

HRID 389052Notes

Reaction equation

HRID 389052 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:14]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:16])[CH3:15].C[O-].[Na+]>CCO>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][CH2:15][C:14]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 54352082HCID 54352082, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2(chloromethyl)quinoline monohydrochloride (5.0 g, 23.4 mmol) and diethyl acetamidomalonate (10.1 g, 46.7 mmol) in EtOH (60 mL) was added sodium methoxide (3.78 g, 70 mmol). The reaction mixture was heated at reflux for 6 h. The reaction mixture was cooled, filtered, and concentrated. The residue was dissolved in EtOAc (400 mL) and extracted with cold 4N HCl (3×150 mL). The aqueous layer was neutralized with 10N NaOH and extracted with EtOAc (3×200 mL). The combined organic extract was washed with water, dried (anhydrous MgSO4), filtered, and concentrated to give the title compound (8.3 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in EtOAc (400 mL)
  7. extractionextracted with cold 4N HCl (3×150 mL)
  8. extractionextracted with EtOAc (3×200 mL)
  9. extractionThe combined organic extract
  10. washwas washed with water
  11. dry with materialdried (anhydrous MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-9672b484ff3a44d98b512f20d5dd5849
Source dataset
uspto-grants-2013_02
Patent number
US08378099B2

Reaction notes

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