Hydrochloric Acid → HCID 78319096, compound

HRID 516595Notes

Reaction equation

HRID 516595 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])=[CH:13][CH:12]=2)[N:7]=[C:6]([C:18]([O:20]C)=[O:19])[C:5]=1[Cl:22].Cl>CO>[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=2)[N:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]=1[Cl:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90409982HCID 90409982, compound

Product 1

HCID 78319096HCID 78319096, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A 2 M solution of sodium hydroxide (740 μL, 1.5 mmol, 4.0 equiv) was added to a stirred solution of methyl 4-amino-6-(4-iodophenyl)-3-chloro-5-fluoropicolinate (150 mg, 0.37 mmol, 1.0 equiv) in methanol (3.7 mL) at 23° C. The resulting pink solution was stirred at 23° C. for 3 h. The reaction mixture adjusted to pH 3, using concentrated hydrochloric acid, and concentrated by rotary evaporation. The residue was slurried in water and vacuum filtered to afford the title compound as a pale pink powder (110 mg, 79%).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. filtrationvacuum filtered

Sources & evidence

ORD record
ord-985188fa0c774fab9c53f51ccd069e81
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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