Hydrochloric Acid → HCID 57950214, compound

HRID 1907673Notes

Reaction equation

HRID 1907673 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][N:16]=1.Cl>O1CCOCC1.[Cu](Cl)Cl.C(OCC)(=O)C.O>[Cl:21][C:20]1[C:15]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 169882,3-DichloropyridineHCID 24758Sodium hydride

Product 1

HCID 57950214HCID 57950214, compoundYield 17.4%

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

8.73 g of sodium hydride (55% oil dispersion) was suspended in 100 ml of 1,4-dioxane. Into this, 32.03 g of diethyl malonate was added dropwise over a period of about 1 hour at 60° C. under a nitrogen atmosphere. The mixture was stirred at the same temperature further for 0.5 hours, then, to the mixture was added 8.26 g of copper chloride (I). Thereafter, into the mixture, a solution prepared by dissolving 12.23 g of 2,3-dichloropyridine in 50 ml of 1,4-dioxane was added dropwise at 80° C. The mixture was stirred for 22.5 hours under reflux with heating. The reaction mixture was allowed to cool to room temperature, and to the reaction mixture was added 15 ml of concentrated hydrochloric acid. To the mixture were added water and ethyl acetate, and the mixture was filtrated through celite. The filtrate was liquid-separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 46.65 g of the resultant residue was subjected to silica gel column chromatography, to obtain 3.90 g of diethyl (3-chloro-2-pyridyl)malonate.

Workup

  1. customThereafter, into the mixture, a solution prepared
  2. additionwas added dropwise at 80° C
  3. stirringThe mixture was stirred for 22.5 hours
  4. temperatureunder reflux
  5. temperaturewith heating
  6. filtrationthe mixture was filtrated through celite
  7. customThe filtrate was liquid-separated
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d9dc7f90de6a4ecd94cc60ee857e9c38
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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