Salicylamide → 2-(Cyclopropylmethoxy)benzamide

HRID 437425Notes

Reaction equation

HRID 437425 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1>C(O)C>[CH:19]1([CH2:18][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([NH2:10])=[O:9])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 27280292-(Cyclopropylmethoxy)benzamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of salicylamide (10.02 g., 0.074 mole), potassium carbonate (10.24 g., 0.074 mole) and bromomethylcyclopropane (10.0 g., 0.074 mole) in ethanol (15 ml.) was heated under reflux for 19 hours. The mixture was concentrated and the residue treated with water. The mixture was filtered and the collected solid recrystallized from benzene-Skellysolve B to give 2-cyclopropylmethoxybenzamide (10.0 g., 71.6%), m.p. 102°-105°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. concentrationThe mixture was concentrated
  4. additionthe residue treated with water
  5. filtrationThe mixture was filtered
  6. customthe collected solid recrystallized from benzene-Skellysolve B

Sources & evidence

ORD record
ord-50e861c7bb06440080c01f334a4704d3
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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