Hydrochloric Acid → HCID 90409876, compound

HRID 516596Notes

Reaction equation

HRID 516596 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[C:13]([F:18])[C:12]=2[F:19])[N:7]=[C:6]([C:20]([O:22]C)=[O:21])[C:5]=1[Cl:24].Cl>CO>[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[C:13]([F:18])[C:12]=2[F:19])[N:7]=[C:6]([C:20]([OH:22])=[O:21])[C:5]=1[Cl:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90408335HCID 90408335, compound

Product 1

HCID 90409876HCID 90409876, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A 2 M solution of aqueous sodium hydroxide (270 L, 0.54 mmol, 2.0 equiv) was added to a stirred suspension of methyl 4-amino-3-chloro-6-(2,3-difluoro-4-iodophenyl)-5-fluoropicolinate (120 mg, 0.27 mmol, 1.0 equiv) in methanol (2.7 mL) at 23° C. The heterogeneous white mixture was stirred at 23° C. for 18 h. The reaction mixture was adjusted to approximately pH 4 via dropwise addition of concentrated hydrochloric acid and concentrated via rotary evaporation. The residue was dissolved in dichloromethane (250 mL), passed through a hydrophobic membrane phase separator, dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation to afford the title compound as a white powder (110 mg, 92%).

Workup

  1. concentrationconcentrated via rotary evaporation
  2. dissolutionThe residue was dissolved in dichloromethane (250 mL)
  3. dry with materialdried (magnesium sulfate), gravity
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e63aecbb8fde459ca23911cce5ac5fb3
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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