Sodium Hydroxide → HCID 90409898, compound

HRID 516590Notes

Reaction equation

HRID 516590 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[C:10]([F:15])[CH:9]=2)[N:5]=[C:4]([C:16]([O:18]C)=[O:17])[C:3]=1[Cl:20].[OH-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[C:10]([F:15])[CH:9]=2)[N:5]=[C:4]([C:16]([OH:18])=[O:17])[C:3]=1[Cl:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90409928HCID 90409928, compound

Product 1

HCID 90409898HCID 90409898, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100-mL round bottom flask, equipped with a stir bar was added methyl 4-amino-3-chloro-6-(3-fluoro-4-iodophenyl)picolinate (0.284 g, 0.699 mmol), 1.0 N sodium hydroxide (2.79 mL, 2.79 mmol) and methanol (5.0 mL). The reaction was allowed to stir for 18 hours at room temperature. The solvent was then removed with a rotary evaporator. The resulting solid was diluted with H2O, which was adjusted to pH-3.0 with 1 N HCl, and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title compound as a white solid (0.056 g, 21%).

Workup

  1. customTo a 100-mL round bottom flask, equipped with a stir bar
  2. customThe solvent was then removed with a rotary evaporator
  3. additionThe resulting solid was diluted with H2O, which
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-152d1546defc4b9aa292bf5feabba55f
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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