Chlorosuccinimide → 2'-acetyl-3-chloro-4-((4-methoxybenzyl)oxy)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

HRID 2199520노트

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HRID 2199520 반응식
[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:12][C:11]2=[O:27])[C:7]([CH3:28])=[CH:6][N:5]=1)(=[O:3])[CH3:2].[Cl:29]N1C(=O)CCC1=O>CC(O)C.ClC(Cl)C(O)=O>[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[C:12]([Cl:29])[C:11]2=[O:27])[C:7]([CH3:28])=[CH:6][N:5]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 31398ChlorosuccinimideHCID 866993052'-Acetyl-4-[(4-methoxyphenyl)methoxy]-5',6-dimethyl[1(2H),4'-bipyridin]-2-one

생성물 1

HCID 866993042'-acetyl-3-chloro-4-((4-methoxybenzyl)oxy)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

시약·촉매·용매 2

HCID 6597Dichloroacetic Acid촉매HCID 3776Isopropanol용매

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온도
60 °C

실험 절차

To a solution of 2′-acetyl-4-((4-methoxybenzyl)oxy)-5′,6-dimethyl-2H-[1,4′-bipyridin]-2-one of part C (689 mg, 1.82 mmol) in 2-propanol (15 mL) was added N-chlorosuccinimide (266 mg, 2.00 mmol) and 3 drops of dichloroacetic acid. The slurry was heated at 60° C. for 3 hours. The solution was cooled using an ice bath and the resulting white solid was collected by vacuum filtration. The filtrate was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was concentrated in vacuo and purified using normal phase chromatography (ethyl acetate/heptane) and the desired product was combined with material obtained via filtration (568 mg): MS (M+H) 414.

후처리

  1. temperatureThe solution was cooled
  2. filtrationthe resulting white solid was collected by vacuum filtration
  3. customThe filtrate was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo
  7. custompurified
  8. customobtained via filtration (568 mg)

출처 및 근거

ORD 기록
ord-d9b9795b37794f49848c23bd5db2cdd3
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359300B2

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