Pyridine → 2-Pyridinecarboxamide

HRID 420463

반응식

HRID 420463 반응식
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].N1C=CC=CC=1.Cl.N1C=CC=CC=1C(Cl)=[O:23]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[N:7]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[C:1]([NH2:8])=[O:23]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7243O-PhenylenediamineHCID 135033Picolinoyl Chloride Hydrochloride

생성물 1

HCID 150702-Pyridinecarboxamide수율 60%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

Dissolving 5.0 g (17 mmol) of (4-bromo-phenyl)-(2-nitrophenyl)-amine into 50 milliliter of tetrahydrofuran, an aqueous solution prepared by dissolving 15 g (86 mmol) of sodium dithionite into 60 milliliter of water was added. Subsequently, adding 10 milliliter of methanol, the resultant solution was stirred at room temperature for 3 hours. After recognizing that the color (orange) of the resultant solution almost disappeared, water was added, followed by extracting with ethyl acetate. After sufficiently drying an organic layer with sodium sulfate, the solvent was removed by distillation, and as a result, phenylenediamine was obtained. Dissolving the resultant phenylenediamine into 150 milliliter of ethyl acetate, an organic layer was extracted. Further, 5.4 g (68 mmol) of pyridine, 3.6 g (23 mmol) of 2-picolinic acid chloride hydrochloride and catalyst amount of 4-dimethylaminopyridine (DMAP) were added to the organic layer, and the resultant solution was stirred at room temperature for 3 hours, followed by left standing for a night. After completion of the reaction, adding water, separation with filtration was carried out for precipitated solids and then, they were sufficiently washed with water and methanol, thereby obtaining 3.8 g of 2-picolinic acid amide as white solid (yield: 60%).

후처리

  1. extractionan organic layer was extracted
  2. waitby left standing for a night
  3. customAfter completion of the reaction
  4. additionadding
  5. customwater, separation
  6. filtrationwith filtration
  7. customfor precipitated solids
  8. washthey were sufficiently washed with water and methanol

출처 및 근거

ORD 기록
ord-ecbca9b7a3d24e138b1f1cf05f63770c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097349B2

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