Malonic Acid → 3-Amino-3-(4-chlorophenyl)propanoic acid

HRID 1823836

Reaktionsgleichung

Reaktionsgleichung von HRID 1823836
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:16]=[CH:15][C:12](C=O)=[CH:11][CH:10]=1.C([O-])(=O)C.[NH4+:21]>C(O)C>[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH:1]([CH2:2][C:3]([OH:5])=[O:4])[NH2:21])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 867Malonic AcidHCID 77264-ChlorobenzaldehydeHCID 517165Ammonium Acetate

Produkt 1

HCID 3441763-Amino-3-(4-chlorophenyl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Malonic acid (7.29 g, 70.0 mmol), 4-chlorobenzaldehye (9.84 g, 70.0 mmol) and ammonium acetate (10.9 g, 140 mmol) were heated in ethanol (15 ml) at 55° C. for 15 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 was extracted with dichloromethane (3×) and the combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a cream solid, 3.48 g.

Aufarbeitung

  1. temperatureUpon cooling the solvent
  2. customwas removed under reduced pressure
  3. extractionThe aqueous was extracted with dichloromethane (3×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b81731f174504855982147da7780c25d
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041667B1

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