Ethyl Salicylate → HCID 19087556, compound

HRID 1464246Notes

Reaction equation

HRID 1464246 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].Cl[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1>CN(C)C=O>[CH2:11]([O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8365Ethyl SalicylateHCID 24758Sodium hydrideHCID 276852,5-Dichloropyridine

Product 1

HCID 19087556HCID 19087556, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl salicylate (30 g, 0.18 mol) was added dropwise with stirring to a suspension of oil-free sodium hydride (5 g, 0.21 mol) in dry dimethylformamide (100 ml) under a nitrogen atmosphere. After one hour, 2,5-dichloropyridine (26 g, 0.17 mol) was added and the reaction mixture refluxed for 48 hours. The dimethylformamide was then removed in vacuo and 11 of a 50:50 (v/v) mixture of water and trichloromethane added to the remaining residue. The organic layer was separated, washed, dried and, finally, chromatographed on a silica column using trichloromethane and hexane (3:1, v/v) as eluant to give the title compound as a colourless oil (32.1 g, 0.115 mol, 64% yield).

Workup

  1. temperaturethe reaction mixture refluxed for 48 hours
  2. customThe dimethylformamide was then removed in vacuo and 11 of a 50:50 (v/v) mixture of water and trichloromethane
  3. additionadded to the remaining residue
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. customfinally, chromatographed on a silica column

Sources & evidence

ORD record
ord-95b032a74852479eae46e744c0fff731
Source dataset
uspto-grants-1994_04
Patent number
US05304532

Reaction notes

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