Phosphorus pentachloride → 3-Chloropyridine-2-carbonitrile

HRID 481746노트

반응식

HRID 481746 반응식
O[C:2]1[C:3]([C:8]([NH2:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12]>P(Cl)(Cl)(Cl)=O>[Cl:12][C:2]1[C:3]([C:8]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 24819Phosphorus pentachlorideHCID 702773-Hydroxypicolinamide

생성물 1

HCID 8182583-Chloropyridine-2-carbonitrile수율 14.9%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

To a solution of 3-hydroxypicolinamide (2.00 g, 14.5 mmol) in phosphorus oxychloride (10 mL) at room temperature was added phosphorus pentachloride (6.00 g, 28.8 mmol). The mixture was heated at reflux for 90 min, and the solvent was removed by distillation. The residue was poured into water, the aqueous solution was neutralized by addition of sodium bicarbonate, and was extracted with ethyl acetate. The organic phase was filtered through silica gel, the filtrate was concentrated, and the residue was subjected to flash chromatography on silica gel, affording 300 mg of 3-chloro-2-cyanopyridine. 1H NMR (CDCl3) δ 7.50 (dd, 1, J=4.8, 8.4), 7.89 (dd, 1, J=1.6, 8.4), 8.63 (dd, 1, J=1.6, 4.8).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 min
  3. customthe solvent was removed by distillation
  4. additionThe residue was poured into water
  5. additionthe aqueous solution was neutralized by addition of sodium bicarbonate
  6. extractionwas extracted with ethyl acetate
  7. filtrationThe organic phase was filtered through silica gel
  8. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-6dcec9bcf5834d06b65aab66312cdbd2
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789584

반응 노트

불러오는 중…