Dimethylformamide → 6-(Pyridin-3-yloxy)-pyridine-3-carbaldehyde

HRID 78089

反応式

HRID 78089 の反応式
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][N:17]=1>O>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:16]2[N:17]=[CH:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=2)[CH:10]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide3 回HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 27640536-Chloropyridine-3-carbaldehyde

生成物 1

HCID 592551936-(Pyridin-3-yloxy)-pyridine-3-carbaldehyde収率 36%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a suspension of sodium hydride (407 mg, 8.48 mmol, 50% in oil) and N,N-dimethylformamide (45 mL) was added an N,N-dimethylformamide (5 mL) solution of 3-hydroxypyridine (806 mg, 8.48 mmol) at 0° C., which was stirred for 30 minutes. An N,N-dimethylformamide (5 mL) solution of 2-chloro-5-formylpyridine (1.0 g, 7.06 mmol) was added to this reaction mixture at the same temperature, which was stirred for 5 hours at 100° C. The reaction mixture was cooled to room temperature, and water was added thereto, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (505.1 mg, 36%).

後処理

  1. stirringwas stirred for 5 hours at 100° C
  2. extractionwhich was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-a48fa208865b4d5b8702eea204cd5d0f
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

読み込み中…