Water → 3-Azido-2-cyanopyridine

HRID 380388Notes

Reaction equation

HRID 380388 reaction equation
Br[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[N-:10]=[N+:11]=[N-:12].[Na+].O>CN(C=O)C>[N:10]([C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1)=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 8176943-Bromopyridine-2-carbonitrile

Product 1

HCID 183650753-Azido-2-cyanopyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-2-cyanopyridine (Chem. Pharm. Bull, 1985, 33, 565) (2.6 g, 14.2 mmol) and sodium azide (1.0 g, 15.3 mmol) in DMF (30 ml) was heated at 90° C. for 16 h. The resulting mixture was cooled, water was added and the whole was extracted with ethyl acetate. The combined extracts were washed with saturated brine and dried over magnesium sulphate. Evaporation of the solvent gave the product as an oil, which was purified by flash column chromatography on silica gel, eluting with ethyl acetate/petrol (1:3 to 1:1) as eluent to afford the product. MS (EI) m/z 145; 1H NMR (d6-DMSO) 8.50 (1H, d), 8.09 (1H, d), 7.77 (1H, dd).

Workup

  1. temperatureThe resulting mixture was cooled
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe combined extracts were washed with saturated brine
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2b638bd9adff4de6b095360425883efb
Source dataset
uspto-grants-2001_10
Patent number
US06303613B1

Reaction notes

Loading…