Water → Methyl 5-cyanopyridine-2-carboxylate

HRID 2045863

Reaction equation

HRID 2045863 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 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).

Workup

  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)

Sources & evidence

ORD record
ord-344dfa946c59497f9c16e874cf959fc2
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Linked notes

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