Methyl Salicylate → N-Butylsalicylamide

HRID 1365585Notes

Reaction equation

HRID 1365585 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:12]([NH2:16])[CH2:13][CH2:14][CH3:15]>CO>[CH2:12]([NH:16][C:1](=[O:10])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 4133Methyl SalicylateHCID 8007Butylamine

Product 1

HCID 93618N-ButylsalicylamideYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.0 g (65.7 mmol) of methyl salicylate and 33 ml of n-butylamine were dissolved in 100 ml of methanol, followed by heating at reflux for 8 hours while stirring. Methanol was distilled off under reduced pressure, and the residue was acidified by adding an aqueous 2 N hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed in turn with water and saturated sodium hydrogen carbonate, and then dried over anhydrous magnesium sulfate. The organic layer was filtered, and the filtrate was concentrated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (eluant hexane/ethyl acetate=10/1 to 5/1) to obtain 10.0 g (yield: 79%) of salicylic acid n-butylamide as an oily substance. 1H—NMR spectrum data of salicylic acid n-butylamide are as follows.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 8 hours
  3. distillationMethanol was distilled off under reduced pressure
  4. additionby adding an aqueous 2 N hydrochloric acid
  5. extractionfollowed by extraction with dichloromethane
  6. washThe organic layer was washed in turn with water and saturated sodium hydrogen carbonate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe organic layer was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (eluant hexane/ethyl acetate=10/1 to 5/1)

Sources & evidence

ORD record
ord-edce66150fc141d598382b73f36e27ed
Source dataset
uspto-grants-2011_02
Patent number
US07892711B2

Reaction notes

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