Acetyl chloride → HCID 90409744, compound

HRID 516573Notes

Reaction equation

HRID 516573 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([F:18])[CH:12]=2)[N:8]=[C:7]([C:19]([O:21][CH3:22])=[O:20])[C:6]=1[Cl:23])(=O)C.C(Cl)(=O)C>CO>[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([F:18])[CH:12]=2)[N:8]=[C:7]([C:19]([O:21][CH3:22])=[O:20])[C:6]=1[Cl:23]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90408910HCID 90408910, compound

Product 1

HCID 90409744HCID 90409744, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100-mL round bottom flask, equipped with a stir bar, was added methyl 4-acetamido-6-(4-bromo-3-fluorophenyl)-3-chloropicolinate (0.411 g, 1.023 mmol), methanol (5.12 mL) and acetyl chloride (1.45 mL, 20.5 mmol). The reaction was allowed to stir at room temperature for 18 hours. The solvent was removed with a rotary evaporator. The resulting solid was dissolved in 1 N NaHCO3 and extracted with ethyl acetate (3×75 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title compound as a white solid (0.324 g, 88%).

Workup

  1. customTo a 100-mL round bottom flask, equipped with a stir bar
  2. customThe solvent was removed with a rotary evaporator
  3. dissolutionThe resulting solid was dissolved in 1 N NaHCO3
  4. extractionextracted with ethyl acetate (3×75 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-36d6f4d413c9494db66e75a9c199d2c0
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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