Hydrochloric Acid → HCID 90410741, compound

HRID 516597Notes

Reaction equation

HRID 516597 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[C:16]([F:17])=[CH:15][C:14]([Br:18])=[C:13]([F:19])[C:12]=2[F:20])[N:8]=[C:7]([C:21]([O:23]C)=[O:22])[C:6]=1[Cl:25])(=O)C.[OH-].[Na+].Cl>C1COCC1.CO.O>[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[C:16]([F:17])=[CH:15][C:14]([Br:18])=[C:13]([F:19])[C:12]=2[F:20])[N:8]=[C:7]([C:21]([OH:23])=[O:22])[C:6]=1[Cl:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90408997HCID 90408997, compound

Product 1

HCID 90410741HCID 90410741, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl 4-acetamido-6-(4-bromo-2,3,6-trifluorophenyl)-3-chloropicolinate (50 mg, 0.122 mmol, 1.0 eq) and sodium hydroxide (14 mg, 0.366 mmol, 3.0 eq) in THF:MeOH:H2O (1:1:0.5, 2.5 mL) was stirred at 20° C. for 2 h. The reaction mixture was acidified to pH 4-5 using 1.5 N HCl and extracted with EtOAc (2×). The combined organic extract was dried over anhydrous Na2SO4 and evaporated to dryness under reduced pressure to provide the title compound as a pale brown solid (30 mg, 65%).

Workup

  1. extractionextracted with EtOAc (2×)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over anhydrous Na2SO4
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ba63b13a110a40c0853a4c92bb459799
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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