Water → Methyl 5-cyanopyridine-2-carboxylate

HRID 1842199

Reaction equation

HRID 1842199 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e37d97c48df7423a8ddbe82b423c4984
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Linked notes

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