Methanol → HCID 67509641, compound

HRID 623449Notes

Reaction equation

HRID 623449 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:22]O>>[Cl:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:15])([F:16])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:22])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 167824855-Chloro-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxylic acid

Product 1

HCID 67509641HCID 67509641, compoundYield 56%

Procedure

A mixture of 5-chloro-6-(2,2,2-trifluoroethoxy)nicotinic acid (5.6 g, 21.9 mmol, Step-1 of Amine-5) and sulfuric acid (0.12 mL, 2.25 mmol) in methanol (40 mL) is refluxed with stirring for 2 days. After removal of the solvent, the residue is poured into 2M sodium hydroxide (100 mL) and extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo to give 3.28 g (56% yield) of the title compound as a white solid.

Workup

  1. temperatureis refluxed
  2. customAfter removal of the solvent
  3. additionthe residue is poured into 2M sodium hydroxide (100 mL)
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de33234e42ce4e25a6fa438ffcd03b7b
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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