Sodium Hydroxide → HCID 90409676, compound

HRID 516594Notes

Reaction equation

HRID 516594 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[C:13]([F:21])[C:12]=2[F:22])[N:8]=[C:7]([C:23]([O:25]C)=[O:24])[C:6]=1[Cl:27])(=O)C.[OH-].[Na+]>CO>[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[C:13]([F:21])[C:12]=2[F:22])[N:8]=[C:7]([C:23]([OH:25])=[O:24])[C:6]=1[Cl:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90409309HCID 90409309, compound

Product 1

HCID 90409676HCID 90409676, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 4-acetamido-3-chloro-6-(2,3-difluoro-4-(trifluoromethyl)phenyl)picolinate (115 mg, 0.28 mmol) in methanol (1 mL) was added 2 Normal (N) aqueous sodium hydroxide solution (NaOH; 1.4 mL, 2.81 mmol). The reaction solution was stirred at ambient temperature for 15 h. The solution was then concentrated, and acidified with a 2 N aqueous HCl solution. The desired product precipitated out of solution. This mixture was extracted (3×) with dichloromethane, the organics were combined, dried (Na2SO4), filtered and the concentrated in vacuo to afford a white solid (94 mg, 90%).

Workup

  1. concentrationThe solution was then concentrated
  2. customThe desired product precipitated out of solution
  3. extractionThis mixture was extracted (3×) with dichloromethane
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe concentrated in vacuo

Sources & evidence

ORD record
ord-97031d2f5d9246189a725b660a4cfa65
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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