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

HRID 2199520ノート

反応式

HRID 2199520 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6597Dichloroacetic Acid触媒HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d9b9795b37794f49848c23bd5db2cdd3
出典データセット
uspto-grants-2016_06
特許番号
US09359300B2

反応ノート

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