Methyl Salicylate → N-Propylsalicylamide

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[CH2:12]([NH2:15])[CH2:13][CH3:14]>>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:15][CH2:12][CH2:13][CH3:14])=[O:6]

Participants

Reactant 2

HCID 4133Methyl Salicylate

HCID 7852Propylamine

Product 1

HCID 81966N-PropylsalicylamideYield 84%

Conditions

Temperature: 80 °C

Procedure

The crude methyl 2-hydroxybenzoate was dissolved in n-propylamine (400 mL). The reaction mixture in a sealed reactor was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography to afford 120 g (84%) of 2-hydroxy-N-propylbenzamide. LCMS ESI (+) m/z 180 (M+1) detected.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give the crude material that
customwas purified by silica gel flash column chromatography

Sources & evidence

ORD record: ord-469bd8986c634922893dbc45d4e96c95
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524702B2

Reaction notes

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