Malonic Acid → HCID 3684868, compound

HRID 1823835Notes

Reaction equation

HRID 1823835 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[Cl:17])C=O.[C:18]([O-])(=O)C.[NH4+:22]>C(O)C>[CH3:18][O:5][C:3](=[O:4])[CH2:2][CH:1]([NH2:22])[C:14]1[CH:11]=[CH:10][C:9]([Cl:8])=[C:16]([Cl:17])[CH:15]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 227103,4-DichlorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 3684868HCID 3684868, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Malonic acid (7.61 g, 73.1 mmol), 3,4-dichlorobenzaldehye (12.5 g, 71.4 mmol) and ammonium acetate (11.2 g, 146.3 mmol) were heated in ethanol (15 ml) at 55° C. for 15 hours. The solvent was removed under reduced pressure and the resulting white solid was suspended in methanolic hydrochloric acid (2.25M, 100 ml) and heated under reflux for 5 hours. Upon cooling the solvent was removed under reduced pressure and the residue was suspended in water and basified to pH 8 using saturated sodium carbonate solution. The aqueous solution was extracted with dichloromethane (3×) and the combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure. The residual brown oil was purified by column chromatography on silica gel using ethyl acetate as eluant to afford the title compound as a cream solid, 5.72 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. temperatureheated
  3. temperatureunder reflux for 5 hours
  4. temperatureUpon cooling the solvent
  5. customwas removed under reduced pressure
  6. extractionThe aqueous solution was extracted with dichloromethane (3×)
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe residual brown oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7b4f5ffe756c427d8f541c846436f8be
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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