Hydrochloric Acid → Ethyl 4-aminomethylsalicylate hydrochloride

HRID 1600395Notes

Reaction equation

HRID 1600395 reaction equation
[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].[CH2:12]([O:11][C:9](=[O:10])[C:8]1[C:7](=[CH:6][C:5]([CH2:4][NH2:1])=[CH:15][CH:14]=1)[OH:16])[CH3:13]

Participants

6

Reactant 3

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

Product 1

HCID 12794728Ethyl 4-aminomethylsalicylate hydrochlorideYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (0.5 g 10% [w/w]) was added to a 1L hydrogenation flaskunder 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 ethyl4-aminomethylsalicylate hydrochloride (m.p. 240°-241° C.).

Workup

  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

Sources & evidence

ORD record
ord-e958b0a1953a43f0ab19cb4abc75250c
Source dataset
uspto-grants-1998_04
Patent number
US05744627

Reaction notes

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