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

HRID 1754661Notes

Reaction equation

HRID 1754661 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-cbc47ed68735417eb1e7e14da0bc3c98
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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