Formic Acid → 5-Bromo-6-chloro-3-pyridinecarboxaldehyde

HRID 1650913Notes

Reaction equation

HRID 1650913 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[N:4][CH:5]=[C:6]([C:8]#N)[CH:7]=1.C(O)=[O:12]>O.C1(C)C=CC=CC=1.[Ni].[Al]>[Br:1][C:2]1[C:3]([Cl:10])=[N:4][CH:5]=[C:6]([CH:8]=[O:12])[CH:7]=1

Participants

6

Reactant 2

HCID 284Formic AcidHCID 229063315-Bromo-6-chloropyridine-3-carbonitrile

Product 1

HCID 223972615-Bromo-6-chloro-3-pyridinecarboxaldehyde

Reagents, catalysts & solvents 3

HCID 6336846Nickel aluminideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3-Bromo-2-chloro-5-cyanopyridine (8.6 g) in 90% formic acid (40 ml) and water (10 ml) were treated with Raney nickel/aluminum alloy (8.0 g) and the mixture stirred and heated to 55°-60° for 6 hours. The mixture was left to stand for two days, and then filtered. The filtrate was diluted to 500 ml with water and extracted with ether (2×250 ml). The ether extract was washed with aqueous sodium carbonate, dried, and evaporated to give an oil. The oil was diluted with toluene which was then removed under reduced pressure. The residue was diluted with a little ether, the solution filtered, and the filtrate evaporated to give an oil identified as the required aldehyde.

Workup

  1. temperatureheated to 55°-60° for 6 hours
  2. waitThe mixture was left
  3. filtrationfiltered
  4. additionThe filtrate was diluted to 500 ml with water
  5. extractionextracted with ether (2×250 ml)
  6. extractionThe ether extract
  7. washwas washed with aqueous sodium carbonate
  8. customdried
  9. customevaporated
  10. customto give an oil
  11. customwas then removed under reduced pressure
  12. additionThe residue was diluted with a little ether
  13. filtrationthe solution filtered
  14. customthe filtrate evaporated
  15. customto give an oil

Sources & evidence

ORD record
ord-45848b3960dc45429aaf63c9ad5df5a7
Source dataset
uspto-grants-1990_05
Patent number
US04925947

Reaction notes

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