Water → N-(2-chloro-5-fluoropyridin-3-yl)-2-methylacrylamide

HRID 385593노트

반응식

HRID 385593 반응식
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.O.[C:11](OCC)(=[O:13])C.N1[CH:22]=[CH:21][CH:20]=CC=1>CC(=C)C(Cl)=O>[Cl:1][C:2]1[C:7]([NH:8][C:11](=[O:13])[C:21]([CH3:20])=[CH2:22])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 8857Ethyl AcetateHCID 447548682-Chloro-5-fluoropyridin-3-amine

생성물 1

HCID 57815236N-(2-chloro-5-fluoropyridin-3-yl)-2-methylacrylamide

시약·촉매·용매 1

HCID 13528Methacryloyl chloride용매

실험 절차

To a solution of 1.2 g of 2-chloro-5-fluoropyridin-3-amine in 5 mL of pyridine, 0.86 mL of 2-methylacryloyl chloride was added under cooling with ice, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, water and ethyl acetate were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate=100:0 to 50:50 to obtain 1.1 g of N-(2-chloro-5-fluoropyridin-3-yl)-2-methylacrylamide as a colorless oily substance.

후처리

  1. temperatureunder cooling with ice
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed sequentially with water
  5. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by flash silica gel column chromatography
  8. washelution with hexane

출처 및 근거

ORD 기록
ord-77d63505f368418782c6ce99173f7ae3
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367831B2

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