Water → Methyl 5-cyanopyridine-2-carboxylate

HRID 2045863

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HRID 2045863 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 h. Water was added to the reaction solution at RT, and the insoluble matter was removed by filtration. The filtrate was extracted with EtOAc. The extract was washed with a saturated NaCl solution and then dried over anhydrous MgSO4. 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 (EtOAc-heptane system) to obtain the title compound (920 mg). 1H-NMR (400 MHz, CDCl3) δ (ppm): 4.06 (s, 3H), 8.16 (dd, J=2.0, 8.0 Hz, 1H), 8.27 (d, J=8.0 Hz, 1H), 9.01 (d, J=2.0 Hz, 1H).

후처리

  1. temperaturewas heated
  2. customthe insoluble matter was removed by filtration
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe extract was washed with a saturated NaCl solution
  5. dry with materialdried over anhydrous MgSO4
  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 (EtOAc-heptane system)

출처 및 근거

ORD 기록
ord-344dfa946c59497f9c16e874cf959fc2
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592408B2

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