Ethanol → 5-Chloro-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

HRID 1480072Notes

Reaction equation

HRID 1480072 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:4]C(C#N)=[N:6][CH:7]=1.[OH-:16].[K+].[CH2:18]([OH:20])[CH3:19]>C(OC(=O)C)C>[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:4][C:19]([C:18]([OH:16])=[O:20])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 902038885-Chloro-4-(2,2,2-trifluoroethoxy)picolinonitrile

Product 1

HCID 902040145-Chloro-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-Chloro-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carbonitrile (Example 24b, 800 mg, 3.38 mmol) in ethanol (10 ml) was added 4.0M aqueous solution of potassium hydroxide (4.65 ml, 18.6 mmol). The reaction was stirred for 30 min at 90° C. under microwave radiation. The reaction mixture was diluted with ethylacetate, poured into a separatory funnel and extracted with 1N aqueous solution hydrochloric acid. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness to yield a crude product (540 mg, 62.5%) which was used without any further purification. MS (ESI, m/z): 256.4 (M+H+).

Workup

  1. additionpoured into a separatory funnel
  2. extractionextracted with 1N aqueous solution hydrochloric acid
  3. customThe organic phase was collected
  4. dry with materialdried over sodium sulfate
  5. customevaporated down to dryness

Sources & evidence

ORD record
ord-57b71de2b8aa46fcad80e62e5a3db794
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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