Methanol → HCID 18974747, compound

HRID 2393238Notes

Reaction equation

HRID 2393238 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH2:22](N(CC)CC)C.CO>O.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH3:22])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 18974752HCID 18974752, compound

Product 1

HCID 18974747HCID 18974747, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 6-[(2-chloro-4-pyridyl)oxy]picolinic acid (28 g, 0.11 mol) and thionyl chloride (50 mL) is refluxed for two hours and concentrated in vacuo to remove residual thionyl chloride. A solution of the resultant acid chloride in ethyl acetate is cooled, treated with triethylamine (55 mL, 0.4 mol) and anhydrous methanol (5.4 mL, 0.13 mol), stirred at room temperature for three hours, and diluted with water. The organic layer is separated, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and a 1:1 hexane/ethyl acetate solution gives the title product as light green crystals (18.1 g, 62.3%, mp 89° C.).

Workup

  1. temperatureis refluxed for two hours
  2. concentrationconcentrated in vacuo
  3. customto remove residual thionyl chloride
  4. temperatureA solution of the resultant acid chloride in ethyl acetate is cooled
  5. customThe organic layer is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a residue

Sources & evidence

ORD record
ord-f7c45a2f09904ffb84aa780e89fbf42d
Source dataset
uspto-grants-1998_09
Patent number
US05807804

Reaction notes

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