Sodium Hydroxide → 3-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid

HRID 887872Notes

Reaction equation

HRID 887872 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[N:6]=1)=[O:4].[OH-].[Na+].O1CCOCC1>CO>[NH2:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 673834083-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 584423403-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (0.9 g, 2.465 mmol) was suspended in MeOH (15 ml) and NaOH 2M (2.465 ml, 4.93 mmol) was added under stirring. 1,4-Dioxane (15.00 ml) was added and the solution was left standing at RT over night. The solvent was removed in vacuo and the resulting residue was dissolved in water (10 ml) and carefully acidified to pH4 with slow addition of 2M HCl (2 ml) whilst stirring. The mixture was extracted with EtOAc (20 ml) and the organic portion was washed with brine and concentrated in vacuo. The residue was purified by reverse phase chromatography (130 g C18 column) eluting with water/MeOH to afford the title compound; LS-MS Rt=1.57 mins[M+H]+ 351.0 (Method 2 min LC_v002).

Workup

  1. waitthe solution was left
  2. waitstanding at RT over night
  3. customThe solvent was removed in vacuo
  4. dissolutionthe resulting residue was dissolved in water (10 ml)
  5. additioncarefully acidified to pH4 with slow addition of 2M HCl (2 ml)
  6. stirringwhilst stirring
  7. extractionThe mixture was extracted with EtOAc (20 ml)
  8. washthe organic portion was washed with brine
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by reverse phase chromatography (130 g C18 column)
  11. washeluting with water/MeOH

Sources & evidence

ORD record
ord-151bc11d0f5e40139eeb0c1b2f385728
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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