Triethylamine → Methyl 5-fluoro-2-isobutyramidobenzoate

HRID 1912517Notes

Reaction equation

HRID 1912517 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](Cl)(=[O:17])[CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C>O1CCCC1>[F:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 2783401Methyl 2-amino-5-fluorobenzoate

Product 1

HCID 60787955Methyl 5-fluoro-2-isobutyramidobenzoateYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-amino-5-fluorobenzoate (alfa) (16.9 g, 100 mmol) and isobutyryl chloride (21.2 g, 200 mmol) in dry tetrahydrofuran was added triethylamine (40.4 g, 400 mmol) at 0° C., then the mixture was stirred at room temperature overnight. After removal of the solvent under reduced pressure, the mixture was suspended in water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was recrystallized from ethyl acetate/petroleum ether (5:1, 150 mL) to give the title compound as white solid (12.3 g, 51.5%).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was recrystallized from ethyl acetate/petroleum ether (5:1, 150 mL)

Sources & evidence

ORD record
ord-6981fc5d7a714180ae5e3ee2e7db9fe7
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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