Sulfuric Acid → 1-(5-Fluoropyridin-2-yl)cyclopropane-1-carboxylic acid

HRID 1805243Notes

Reaction equation

HRID 1805243 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(C#N)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.S(=O)(=O)(O)O.[C:18]([O-:21])(O)=[O:19].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:18]([OH:21])=[O:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 671516421-(5-Fluoropyridin-2-yl)cyclopropane-1-carbonitrile

Product 1

HCID 671515151-(5-Fluoropyridin-2-yl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-fluoropyridin-2-yl)cyclopropanecarbonitrile (880 mg) was dissolved in ethanol (10 ml) before slow, dropwise addition of 96% sulfuric acid (10 ml). The reaction mixture was allowed to stir at 60° C. for 24 hr. Upon cooling, NaHCO3 was added until pH 8 and then the solution extracted three times with ethyl acetate, the organics were washed with brine and dried over Na2SO4 before concentration in vacuo.

Workup

  1. temperatureUpon cooling
  2. extractionthe solution extracted three times with ethyl acetate
  3. washthe organics were washed with brine
  4. dry with materialdried over Na2SO4 before concentration in vacuo

Sources & evidence

ORD record
ord-1dd0fff8c6ab4e92b1c52d6675fd1d8f
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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