Hydrochloric Acid → 6-Bromo-3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)picolinic acid

HRID 887862Notes

Reaction equation

HRID 887862 reaction equation
C[O:2][C:3]([C:5]1[C:10]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:9][C:8]([C:18]([F:21])([F:20])[F:19])=[C:7]([Br:22])[N:6]=1)=[O:4].[OH-].[Na+].O.Cl>C1COCC1>[Br:22][C:7]1[N:6]=[C:5]([C:3]([OH:4])=[O:2])[C:10]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:9][C:8]=1[C:18]([F:20])([F:19])[F:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 584423696-Bromo-3-(2,5-dimethyl-pyrrol-1-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 866576686-Bromo-3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Bromo-3-(2,5-dimethyl-pyrrol-1-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.9 g, 5.04 mmol) and 2M NaOH (2.52 ml, 5.04 mmol) in THF (10 ml) was stirred at RT for 1 hour. The reaction mixture was poured into water (50 ml) and the pH was adjusted to pH 4 by addition of 1M HCl. The mixture was extracted with EtOAc (2×50 ml) and the organic portion was washed with brine (30 ml), dried over MgSO4 (5 g), filtered and concentrated to give the title compound as a crystalline orange solid;

Workup

  1. extractionThe mixture was extracted with EtOAc (2×50 ml)
  2. washthe organic portion was washed with brine (30 ml)
  3. dry with materialdried over MgSO4 (5 g)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a57a0378ef7b471da1fe25afc3b1b86f
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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