Pyridine → Methyl 3-benzamido-2-fluorobenzoate

HRID 534666Notes

Reaction equation

HRID 534666 reaction equation
Cl.[NH2:2][C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].N1C=CC=CC=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([NH:2][C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 67167731Methyl 3-amino-2-fluorobenzoate hydrochloride

Product 1

HCID 58298651Methyl 3-benzamido-2-fluorobenzoateYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-amino-2-fluorobenzoate hydrochloride (7.77 g, 0.037 mol) was suspended in methylene chloride (100 ml), and pyridine (6.94 g, 0.085 mol) was added dropwise thereto. Benzoyl chloride (5.78 g, 0.041 mol) was added dropwise to this reaction mixture under cooling, and the mixture was agitated overnight at room temperature. After completion of the reaction, the reaction mixture was washed sequentially with a 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and the reaction mixture was dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and then the filtrate was concentrated under reduced pressure. The concentration residue was recrystallized from ethyl acetate, as a result of which 8.79 g (yield: 85%) of the indicated compound was obtained.

Workup

  1. temperatureunder cooling
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed sequentially with a 1N hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium bicarbonate, and saturated saline, and the reaction mixture was dried over anhydrous sodium sulfate
  5. filtrationThe sodium sulfate was filtered away
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe concentration residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-79e8d02fb53140d0b0beb752492f9846
Source dataset
uspto-grants-2014_10
Patent number
US08853440B2

Reaction notes

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