Water → Methyl 5-cyanopyridine-2-carboxylate

HRID 1693167

反応式

HRID 1693167 の反応式
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]

参加物

5

反応物 3

HCID 962WaterHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 178418260HCID 178418260、化合物

生成物 1

HCID 45082467Methyl 5-cyanopyridine-2-carboxylate収率 43.8%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
170 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-984cf9eee2a84d82874efe1cce27c57b
出典データセット
uspto-grants-2012_04
特許番号
US08158620B2

関連ノート

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