Potassium Carbonate → 3-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

HRID 1800422ノート

反応式

HRID 1800422 の反応式
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([OH:20])[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 673114233-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide

生成物 1

HCID 684192063-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide収率 99%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide (3.11 g, 10.1 mmol) and 2-chloro-5-nitropyridine (1.60 g, 10.1 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (4.24 g, 30.7 mmol), and the mixture was stirred at 60° C. for 16 hr. The reaction solution was cooled to room temperature, and diluted with a mixed solvent (250 mL) of ethyl acetate and hexane (1:1). The solution was washed with water (200 mL×3), and the combined m aqueous layer was extracted with a mixed solvent (100 mL×3) of ethyl acetate and hexane (1:1). The combined organic layer was washed with saturated brine (100 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (4.3 g, 99%) as pale-yellow crystals.

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. washThe solution was washed with water (200 mL×3)
  3. extractionthe combined m aqueous layer was extracted with a mixed solvent (100 mL×3) of ethyl acetate and hexane (1:1)
  4. washThe combined organic layer was washed with saturated brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a9ec3eea055746dd9079826875978ee8
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

読み込み中…