Methanol → Methyl 6-chloro-2-methoxynicotinate

HRID 386020Notes

Reaction equation

HRID 386020 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](F)[N:3]=1.[CH3:13][O-:14].[Na+].CO>>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:14][CH3:13])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 59526352Methyl 6-chloro-2-fluoronicotinate

Product 1

HCID 10560015Methyl 6-chloro-2-methoxynicotinate

Procedure

Methyl 6-chloro-2-fluoronicotinate (Example 454, Step 1) (76 mg, 0.40 mmol) was taken up in a 0.5 M solution of sodium methoxide in methanol (0.80 ml, 0.40 mmol) and stirred at room temperature for 3 hours. The mixture was quenched with saturated aqueous ammonium chloride and extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-17% ethyl acetate/hexanes) to afford the title compound as a white solid.

Workup

  1. customThe mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified via flash chromatography (silica, 0-17% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4b563ced17b14a9bb0239e894d1dfb8a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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