Water → 2,6-Difluoro-nicotinic acid methyl ester

HRID 1024183Notes

Reaction equation

HRID 1024183 reaction equation
[F:1][C:2]1[N:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.O.[C:18](=O)([O-])[O-].[K+].[K+]>CO>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:11])=[N:10][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 105830702,6-Difluoropyridine-3-carboxylic acid

Product 1

HCID 108449402,6-Difluoro-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2,6-difluoro-nicotinic acid (59, 5.60 g, 0.0352 mol) in methanol (60.0 mL) was added concentrated sulfuric acid (1.0 mL, 0.019 mol). The reaction was heated to reflux overnight, then poured into water, basified with 1M potassium carbonate to pH around 9, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give a yellow oil (60, 3.5 g, 57.0%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give a yellow oil (60, 3.5 g, 57.0%)

Sources & evidence

ORD record
ord-457d5bb45a014f8c8eb941300a3b354c
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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