Diethyl Malonate → HCID 57619613, compound

HRID 545294Notes

Reaction equation

HRID 545294 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7]CC)=O.[Cl:14][C:15]1[C:20](=O)[O:19][C:18](=O)[N:17](C)[C:16]=1[CH3:24]>O1CCCC1>[Cl:14][C:15]1[C:20]([OH:19])=[C:4]([C:3]([O:11][CH2:12][CH3:13])=[O:10])[C:5](=[O:7])[N:17]([CH3:18])[C:16]=1[CH3:24]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 576721385-Chloro-3,4-dimethyl-2H-1,3-oxazine-2,6(3H)-dione

Product 1

HCID 57619613HCID 57619613, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 0.43 g of sodium hydride (60%) was added 35 ml of tetrahydrofuran, 2.5 ml of a solution of 1.76 g diethyl malonate in tetrahydrofuran was further added under ice cooling, and the mixture was stirred at room temperature for 1 hour. To the mixture was added 1.74 g of 5-chloro-3,4-dimethyl-2H-1,3-oxazine-2,6(3H)-dione, and this was stirred for 3.5 hours under heat refluxing condition. The reaction mixture was concentrated under reduced pressure. To the residue, 20 ml of water and 15 ml of 1 mol/L hydrochloric acid were sequentially added, followed by extraction with 85 ml of chloroform twice. The organic layer was dried with magnesium sulfate, filtered, and concentrated. The residue was washed with n-hexane to obtain 1.52 g of ethyl 5-chloro-1.6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate represented by the formula:

Workup

  1. additionwas further added under ice cooling
  2. stirringthis was stirred for 3.5 hours
  3. temperatureunder heat
  4. temperaturerefluxing condition
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionTo the residue, 20 ml of water and 15 ml of 1 mol/L hydrochloric acid were sequentially added
  7. extractionfollowed by extraction with 85 ml of chloroform twice
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-1376f6c1d69e4dfa88335c6e6cd39580
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

Loading…