Hydrochloric Acid → Ethyl 4-aminomethylsalicylate hydrochloride

HRID 342828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342828
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([OH:16])[C:8](=[CH:14][CH:15]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+]=[N-].[ClH:17].[H][H]>[Pd].C(O)C>[ClH:17].[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([OH:16])[C:8](=[CH:14][CH:15]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 22556088Ethyl 4-azidomethylsalicylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 12794728Ethyl 4-aminomethylsalicylate hydrochlorideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Palladium on carbon (0.5 g, 10% [w/w]) was added to a 1L hydrogenation on flask under a nitrogen atmosphere. The crude ethyl 4-azidomethylsalicylate was dissolved in ethanol (200 mL) and transferred to the hydrogenation flask. Concentrated aqueous hydrochloric acid (2 mL) was then added, and the flask was affixed to the Parr hydrogenator. The reaction mixture was shaken under 35 psi of hydrogen for 4 hours at room temperature. The mixture was then filtered through Celite to remove the catalyst, and the filtrate was evaporated to dryness to afford an off-white solid. Finally, this solid was crystallized from EtOH to afford 3.1 g (71% yield) of ethyl 4-aminomethylsalicylate hydrochloride (m.p. 240°-241° C.).

Aufarbeitung

  1. filtrationThe mixture was then filtered through Celite
  2. customto remove the catalyst
  3. customthe filtrate was evaporated to dryness
  4. customto afford an off-white solid
  5. customFinally, this solid was crystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-edc09abb6c4941dc8e11e3dfb99216b4
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859210

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