Hydrogen Peroxide → 6-(4-Formylphenoxy)pyridine-3-carboxamide

HRID 131045ノート

反応式

HRID 131045 の反応式
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=[O:19].[K+].[K+].OO>CS(C)=O>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:19])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=[O:2]

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 471502166-(4-Formylphenoxy)nicotinonitrile

生成物 1

HCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide収率 171.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Combine 6-(4-Formyl-phenoxy)-nicotinonitrile (3.02 g, 13.5 mmol), powdered K2CO3 (0.93 g, 6.7 mmol), and DMSO (100 mL) in a RB flask and add H2O2, 30% wt. Aq (4.05 mL, 13.5 mmol) by dropwise addition at 0° C. Stir the reaction mixture for 3 hours allowing it to come to room temperature then quench the reaction slowly at 0° C. with water. Extract the product out of the water layer with ethyl acetate several times and then wash with brine. Dry over Na2SO4 and concentrate under reduced pressure to give 2.78 g (95% yield) of the title compound: 1H NMR (500 MHz, DMSO); 7.2 (1H, d), 7.3-7.4 (2H, m), 7.5 (1H, br s), 7.9-8.0 (2H, m), 8.1 (1H, br s), 8.3 (1H, d), 8.7 (1H, s), 10.0 (1H, s); MS m/z 243 (M+1).

後処理

  1. additionby dropwise addition at 0° C
  2. customto come to room temperature
  3. customthen quench
  4. customthe reaction slowly at 0° C. with water
  5. extractionExtract the product out of the water layer with ethyl acetate several times
  6. washwash with brine
  7. dry with materialDry over Na2SO4
  8. concentrationconcentrate under reduced pressure

出典と根拠

ORDレコード
ord-17ca114b68ef4829bfe082eacac8e519
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

反応ノート

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