Pyridine → Methyl 3-benzamido-2-fluorobenzoate

HRID 534666ノート

反応式

HRID 534666 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 58298651Methyl 3-benzamido-2-fluorobenzoate収率 86.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-79e8d02fb53140d0b0beb752492f9846
出典データセット
uspto-grants-2014_10
特許番号
US08853440B2

反応ノート

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