Acetic Acid → 5-(2-Amino-1-hydroxyethyl)-2-hydroxybenzamide

HRID 1701857Notes

Reaction equation

HRID 1701857 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][C:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([OH:21])=[CH:14][CH:13]=1)=[O:11])C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[NH2:8][CH2:9][CH:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([OH:21])=[CH:14][CH:13]=1)[OH:11]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1217275-((Bis(benzyl)amino)acetyl)salicylamide

Product 1

HCID 155656635-(2-Amino-1-hydroxyethyl)-2-hydroxybenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 5-[2-(dibenzylamino)acetyl]salicylamide (75.0 g, 0.200 mmol) and acetic acid (24.0 g, 0.40 mmol) in 1.0 liter methanol, add 5% palladium/carbon (40.0 g). Hydrogenate at 3 atmospheres for 16 hours. Filter the catalyst, concentrate slightly and adjust the volume to give a solution of the title compound of the desired molarity.

Workup

  1. filtrationFilter the catalyst
  2. concentrationconcentrate slightly

Sources & evidence

ORD record
ord-33d75df1d5c5406ba7463d52e13ff989
Source dataset
uspto-grants-1983_04
Patent number
US04379166

Reaction notes

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