Water → Methyl 5-cyanopyridine-2-carboxylate

HRID 1693167

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HRID 1693167 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[Cu](C#N)[C:13]#[N:14].O>CN1C(=O)CCC1>[C:13]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)#[N:14]

참가 물질

5

반응물 3

HCID 962WaterHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 45082467Methyl 5-cyanopyridine-2-carboxylate수율 43.8%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
170 °C

실험 절차

A mixture of methyl 5-bromopyridine-2-carboxylate (2.8 g) and copper cyanide (3.6 g) in NMP (30 mL) was heated with stirring at 170° C. for 1.5 hours. Water was added to the reaction solution at room temperature, and the insoluble matter was removed by filtration. The filtrate was extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate-heptane system) to obtain the title compound (920 mg).

후처리

  1. temperaturewas heated
  2. customthe insoluble matter was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate-heptane system)

출처 및 근거

ORD 기록
ord-984cf9eee2a84d82874efe1cce27c57b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158620B2

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