Pyridine → Methyl 3-benzamido-2-fluorobenzoate

HRID 1053613노트

반응식

HRID 1053613 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b81dc60a4784cc585d33b09d7b5d44f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394240B2

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