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

HRID 131045노트

반응식

HRID 131045 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide수율 171.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-17ca114b68ef4829bfe082eacac8e519
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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