Hydrochloric Acid → 4-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carboxylic acid

HRID 1426330Notes

Reaction equation

HRID 1426330 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([C:14]#N)[CH:5]=1.[OH-:16].[Na+].[OH2:18].Cl>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([C:14]([OH:18])=[O:16])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 696735024-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 696732854-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(methoxymethyl)-6-(trifluoromethyl)pyridine-2-carbonitrile (0.36 g, 1.7 mmol, from Step C) in ethanol (20 mL) was added 1.0M sodium hydroxide in water (6.5 mL, 6.5 mmol) and the reaction was heated in an oil bath held at 90° C. for 4 hours. Upon cooling to room temperature, 1N HCl was added to achieve pH 2, and the product was extracted with ethyl acetate (3×). The combined extracts were dried over sodium sulfate, decanted and concentrated to afford a crystalline solid which was used without further purification. 1H NMR (300 MHz, CD3OD) δ 8.29 (s, 1H), 7.95 (s, 1H), 4.66 (s, 2H), 3.49 (s, 3H); 19F NMR (282 MHz, CD3OD) δ−69.56 (s); LCMS (M+H)+: 236.0.

Workup

  1. temperaturethe reaction was heated in an oil bath
  2. extractionthe product was extracted with ethyl acetate (3×)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated
  6. customto afford a crystalline solid which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-70c070e8d747418088ffb47a6aac9a31
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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