Sodium Hydroxide → HCID 58073847, compound

HRID 1470660Notes

Reaction equation

HRID 1470660 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[C:9]([F:10])=[C:8]([F:11])[C:7]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:18])=[C:6]([F:19])[C:5]=1[F:20].[OH-].[Na+]>C1COCC1>[CH3:18][C:13]1[N:12]([C:7]2[C:8]([F:11])=[C:9]([F:10])[C:4]([C:3]([OH:21])=[O:2])=[C:5]([F:20])[C:6]=2[F:19])[C:16]([CH3:17])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58073907HCID 58073907, compound

Product 1

HCID 58073847HCID 58073847, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To the solution of 4-(2,5-dimethyl-pyrrol-1-yl)-2,3,5,6-tetrafluoro-benzoic acid methyl ester (0.6 g, 1.99 mmol) in THF (20 mL) was added an aq. solution of 5 N NaOH (5 mL). The reaction mixture was stirred under refluxed at 90° C. for 3 hours. TLC shows completion of the reaction. The reaction mixture was concentrated and the resulting residue was cooled, acidified with aq, solution of 2 N HCl, extracted with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous sodium sulphate then concentrated. The resulting residue was purified by washing with hot hexane to get the title compound (0.43 g, 75%). LCMS− m/z 288, 91%

Workup

  1. customcompletion of the reaction
  2. concentrationThe reaction mixture was concentrated
  3. temperaturethe resulting residue was cooled
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationthen concentrated
  8. customThe resulting residue was purified
  9. washby washing with hot hexane

Sources & evidence

ORD record
ord-78ef8a77de0148a5a4cf7586d08c367c
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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