Sodium Hydroxide → 5-Bromopyridine-2-carbonitrile

HRID 72394

Reaction equation

HRID 72394 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH2:15])=O)=[N:11][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:15])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 7351515-Bromopyridine-2-carboxamide

Product 1

HCID 8171545-Bromopyridine-2-carbonitrileYield 82.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus oxychloride (111 g, 0.720 mol) was added to a mixture of 5-bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300 ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1. Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1
  8. customCollected fractions, after solvent evaporation

Sources & evidence

ORD record
ord-e83cf6404d21478aac0b005324c1ef0e
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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