Salicylamide → 2-(Cyclopropylmethoxy)benzamide

HRID 1030494Notes

Reaction equation

HRID 1030494 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[K+].[CH:13]1([CH2:16]Br)[CH2:15][CH2:14]1>C(O)C>[CH:13]1([CH2:16][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([NH2:10])=[O:9])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 14797Potassium HydroxideHCID 81503Bromomethylcyclopropane

Product 1

HCID 27280292-(Cyclopropylmethoxy)benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Salicylamide (15.22 g), potassium hydroxide (85%, 7.73 g) and cyclopropylmethyl bromide (16.024 g) were heated together under reflux in absolute ethanol (100 ml) for 91/2 hours. The cooled mixture was filtered to remove inorganic products and the filtrate was evaporated to an oil. The oil was dissolved in 1:1 toluene:ethyl acetate (200 ml) and the solution was washed with 10% potassium hydroxide solution (2×30 ml), water (50 ml) and saturated brine (50 ), dried (Na2SO4), and concentrated under reduced pressure, leaving 2-(cyclopropylmethoxy)benzamide as an oil which crystallised (17.606 g, 83%), mp 95°-100° C.

Workup

  1. filtrationThe cooled mixture was filtered
  2. customto remove inorganic products
  3. customthe filtrate was evaporated to an oil
  4. dissolutionThe oil was dissolved in 1:1 toluene
  5. washethyl acetate (200 ml) and the solution was washed with 10% potassium hydroxide solution (2×30 ml), water (50 ml) and saturated brine (50 )
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d486e383ce8148c69dfcb0b8c369f281
Source dataset
uspto-grants-1992_04
Patent number
US05106843

Reaction notes

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