Sulfuric Acid → 5-(2-Benzylaminopropoxy)salicylamide

HRID 4554

Reaction equation

HRID 4554 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 conc. sulfuric acid are added to a solution of 104.5 g of 5-(2-oxo-propoxy)salicylamide in 1000 ml of methanol, and the mixture is hydrogenated, in the presence of 3.0 g of a Pt/C catalyst under normal conditions until 1 equivalent of hydrogen has been absorbed. The catalyst is filtered off, and the solution is then stirred up with about 10 g of pulverised calcium carbonate; the mixture is again filtered, and concentrated by evaporation. The oil remaining behind crystallises from isopropanol. Repeated recrystallisation from isopropanol yields 5-[2-(benzylamino)-propoxy]-salicylamide, m.p. 102°-104°.

Workup

  1. customhas been absorbed
  2. filtrationThe catalyst is filtered off
  3. filtrationthe mixture is again filtered
  4. concentrationconcentrated by evaporation
  5. custombehind crystallises from isopropanol
  6. customrecrystallisation from isopropanol

Sources & evidence

ORD record
ord-fd0ebe5400be4198acdf81230619e204
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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