Sodium Azide → 4-Azido-5-chloropyridine-3-carbaldehyde

HRID 626705Notes

Reaction equation

HRID 626705 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10])=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 595965804,5-Dichloropyridine-3-carbaldehyde

Product 1

HCID 866970494-Azido-5-chloropyridine-3-carbaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-dichloropyridine-3-carbaldehyde (6.78 g, 38.5 mmol) and sodium azide (2.62 g, 40.4 mmol) in DMF (25 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (250 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane) to afford the title compound as a yellow solid (6.7 g, 96% yield). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 8.84 (s, 1H), 8.65 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with brine (250 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-6bfcfd0dc6364ef3a2a4de86f0e0f2bc
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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