Sodium Hydroxide → 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinic acid

HRID 444933Notes

Reaction equation

HRID 444933 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[C:9]([C:21]([O:23]C)=[O:22])=[N:10][C:11]([O:18][CH2:19][CH3:20])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-].[Na+]>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[C:9]([C:21]([OH:23])=[O:22])=[N:10][C:11]([O:18][CH2:19][CH3:20])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67383877Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinate

Product 1

HCID 584423293-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinate (140 mg, 0.409 mmol) was dissolved in THF (2.045 ml). NaOH (0.613 ml, 1.226 mmol) was added and heated at reflux for 6 hours. The solvent was removed in vacuo and the resulting mixture was diluted with EtOAc (25 ml) was acidified to pH 1 using HCl (5M). The organic portion washed with brine, dried using a phase separator and concentrated in vacuo to afford the title compound as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was removed in vacuo
  4. additionthe resulting mixture was diluted with EtOAc (25 ml)
  5. washThe organic portion washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c6942f583864470b66b88235d657fb4
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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