Hydrochloric Acid → Ethyl 4-aminomethylsalicylate hydrochloride

HRID 985168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985168
[N:1]([CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:16])[CH:6]=1)=[N+]=[N-].[ClH:17].[H][H]>[Pd].C(O)C>[ClH:17].[NH2:1][CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:16])[CH:6]=1

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 1 L hydrogenation flask under a nitrogen atmosphere. The crude ethyl 4-azidomethyl-2-hydroxybenzoate 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-(aminomethyl)-2-hydroxybenzoate 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-19b7df73ca2247a986aff510f2002641
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06870065B2

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