Methyl Salicylate → N-Methylsalicylamide

HRID 270101

Reaction equation

HRID 270101 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:12][NH2:13]>CO>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:13][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 4133Methyl SalicylateHCID 6329Methylamine

Product 1

HCID 74624N-MethylsalicylamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl salicylate (5.16 mL, 40 mmol) in methanol (10 mL) was added dropwise to aqueous 40% methylamine (18.1 mL, 210 mmol) at 0° C. After addition was complete the reaction mixture was kept on stirring at room temperature overnight. The volatiles were removed in vacuo to give the subtitled compound (5.48 g).

Workup

  1. additionAfter addition
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-6df448f464b946efb1c50dd83b17c1f4
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Linked notes

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