Imidazole → 1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one

HRID 39697ノート

反応式

HRID 39697 の反応式
CN(C)C=O.[H-].[Na+].[NH:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.Br[C:14]1[CH:23]=[C:22]2[C:17]([C:18]([CH3:31])=[CH:19][C:20](=[O:30])[N:21]2[CH2:24][CH:25]2[O:29][CH2:28][CH2:27][O:26]2)=[CH:16][CH:15]=1>[Cu]=O.O.C(Cl)(Cl)Cl>[O:26]1[CH2:27][CH2:28][O:29][CH:25]1[CH2:24][N:21]1[C:22]2[C:17](=[CH:16][CH:15]=[C:14]([N:8]3[CH:12]=[CH:11][N:10]=[CH:9]3)[CH:23]=2)[C:18]([CH3:31])=[CH:19][C:20]1=[O:30]

参加物

8

反応物 4

HCID 795ImidazoleHCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 593980747-Bromo-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1h)-one

生成物 1

HCID 593979121-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one

試薬・触媒・溶媒 3

HCID 14829Copper oxide触媒HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
142.5 °C

実験手順

To 0.7 mL of an N,N-dimethylformamide solution containing 74 mg of 60% sodium hydride, 0.14 g of imidazole was added at room temperature, and the mixture was stirred for 10 minutes. Thereto were added 0.20 g of 7-bromo-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one and 17 mg of copper(II) oxide, and the mixture was heated to 140 to 145° C. and stirred for 40 minutes. Thereto was further added 2 mL of N,N-dimethylformamide, and the mixture was further stirred for 1 hour. The reaction mixture was cooled to room temperature, then chloroform and water were added thereto, and the insoluble material filtered off. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to obtain 77 mg of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one.

後処理

  1. additionwas added at room temperature
  2. stirringstirred for 40 minutes
  3. stirringthe mixture was further stirred for 1 hour
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationthe insoluble material filtered off
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform
  8. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

出典と根拠

ORDレコード
ord-440530fd2e514d4ca5b600297af91348
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

反応ノート

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