Sulfuric Acid → 5-(2-Benzylaminopropoxy)salicylamide

HRID 4524

Reaction equation

HRID 4524 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O=[C:15]([CH3:28])[CH2:16][O:17][C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1.[H][H]>CO.[Pt]>[CH2:1]([NH:8][CH:15]([CH3:28])[CH2:16][O:17][C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7504BenzylamineHCID 137543335-(2-Oxopropoxy)salicylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 137543345-(2-Benzylaminopropoxy)salicylamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

55 g of benzylamine and 1.25 g of concentrated sulphuric acid are added to a solution of 104.5 g of 5-(2-oxopropoxy)salicylamide in 100 ml of methanol and hydrogenated in the presence of 3.0 g of Pt/C-catalyst at room temperature and atmospheric pressure until 1 equivalent of hydrogen has been absorbed. The catalyst is filtered off, approximately 10 g of powdered calcium carbonate are stirred into the solution and the solution is filtered again and concentrated by evaporation. The oil remaining crystallises from isopropanol. Repeated recrystallisation from isopropanol yields 5-[2-(benzylamino)propoxy]salicylamide having a melting point of 102°-104°.

Workup

  1. filtrationThe catalyst is filtered off
  2. filtrationthe solution is filtered again
  3. concentrationconcentrated by evaporation
  4. customThe oil remaining crystallises from isopropanol
  5. customrecrystallisation from isopropanol

Sources & evidence

ORD record
ord-93a5ea0a4f844f3b992c9c05b03c834a
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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