Ethyl Acetate → 4-Azidopyridine-3-carbaldehyde

HRID 626655Notes

Reaction equation

HRID 626655 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[CH:12]=[O:13].C(OCC)(=O)C>CN(C=O)C>[N:1]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[CH:12]=[O:13])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 140466744-Chloropyridine-3-carbaldehyde

Product 1

HCID 866970374-Azidopyridine-3-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (1.07 g, 16.5 mmol) was added to a mixture of 4-chloro-3-formylpyridine (2.22 g, 15.7 mmol) in DMF (15 mL) and the reaction mixture was stirred for 18 hours. Ethyl acetate was added and the organic layers were washed with water and brine. The combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-60% ethyl acetate in cyclohexane) to afford the title compound as a white solid (2.02 g, 87% yield). 1H NMR (300 MHz, CDCl3): δ 10.35 (s, 1H), 8.99 (s, 1H), 8.72 (d, J=5.6 Hz, 1H), 7.20 (d, J=5.6 Hz, 1H).

Workup

  1. washthe organic layers were washed with water and brine
  2. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-60% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-e6e7722ce3434acfb18983a9eee45ef8
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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