Hydrochloric Acid → Ethyl 4-aminomethylsalicylate hydrochloride

HRID 362572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362572
[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].CO>[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 887MethanolLösungsmittel

Versuchsvorschrift

Palladium on carbon (0.5 g; 10% [w/w]) was added to a 1L hydrogenation flask under a nitrogen atmosphere. The crude ethyl 4-azidomethylsalicylate was dissolved in methanol (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-e39124b5dd1d49a897820ab55467828f
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869623

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