Ethanol → Ethyl 2-chloro-6-methoxyisonicotinate

HRID 1436596Notes

Reaction equation

HRID 1436596 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([O:11][CH3:12])[N:10]=[C:2]([Cl:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 27821242-Chloro-6-methoxypyridine-4-carboxylic acid

Product 1

HCID 13611989Ethyl 2-chloro-6-methoxyisonicotinateYield 98%

Conditions

Temperature
70 °C

Procedure

Treat an ethanol suspension of 2-chloro-6-methoxy-isonicotinic acid (3.75 g, 20 mmol) at 0° C. with thionyl chloride for 30 min. Heat at 70° C. overnight. Cool to room temperature, concentrate, dissolve the residue in ethyl acetate (200 mL), wash the organic layer with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution, dry (magnesium sulfate) and concentrate to give the title compound (4.2 g, 98%).

Workup

  1. additionTreat
  2. temperatureCool to room temperature
  3. concentrationconcentrate
  4. dissolutiondissolve the residue in ethyl acetate (200 mL)
  5. washwash the organic layer with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-aa1f1703f0ee4f37aee9a11ffb2751f0
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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