Methyl Salicylate → N-cyclopropyl-2-hydroxybenzamide

HRID 270061Notes

Reaction equation

HRID 270061 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH:12]1([NH2:15])[CH2:14][CH2:13]1>>[CH:12]1([NH:15][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 4133Methyl SalicylateHCID 69828Cyclopropylamine2×

Product 1

HCID 822771N-cyclopropyl-2-hydroxybenzamideYield 53.3%

Conditions

Temperature
90 °C

Procedure

A mixture of of methyl salicylate (4.36 g, 28.69 mmol) and cyclopropylamine (1.64 g) was heated in a sealed tube at 80-100° C. for 3 h. An additional 0.5 g of cyclopropylamine was added and heated at 70° C. overnight. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography to give the subtitled compound (2.71 g).

Workup

  1. temperatureheated at 70° C. overnight
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-e44468fbda1a47d3b1da0faaf04f2832
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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