Salicylamide → 2-Propoxybenzamide

HRID 1413248Notes

Reaction equation

HRID 1413248 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-].[Na+].I[CH2:15][CH2:16][CH3:17]>C(O)C>[CH2:15]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH2:10])=[O:9])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 336431-IodopropaneHCID 10942334Sodium Methoxide

Product 1

HCID 430512-Propoxybenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 130 gm. portion of salicylamide in 500 ml. of ethanol is reacted with 52.4 gm. of sodium methoxide and 164.9 gm. of 1-iodopropane by heating at reflux. The mixture is cooled, precipitated in 1500 ml. of water and the solid is recrystallized from hot ethanol giving o-propoxybenzamide.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture is cooled
  3. customprecipitated in 1500 ml
  4. customof water and the solid is recrystallized from hot ethanol

Sources & evidence

ORD record
ord-54406c68a1c64b7fa2be4b95cccfd99a
Source dataset
uspto-grants-1981_02
Patent number
USRE030511

Reaction notes

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