Sodium Carbonate → 2-Chloro-4-pyridinecarboxaldehyde

HRID 1165764Notes

Reaction equation

HRID 1165764 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.BrN1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 27629942-Chloro-4-pyridinecarboxaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

69.0 g of 2-chloro-4-pyridinemethanol, 128.3 g of N-bromosuccinimide and 101.9 g of anhydrous sodium carbonate were suspended in 1.8 liters of benzene, and refluxed for 4 hours. After cooling, a saturated aqueous solution of sodium hydrogen carbonate was added little by little with stirring until bubbling ceased. The insoluble matter was removed by filtration. The organic layer was separated, washed with a 10% aqueous solution of sodium thiosulfate once and then a saturated aqueous solution of sodium chloride twice, and dried. The solvent was evaporated to give 64.3 g (yield 95%) of 2-chloro-4-pyridinecarboxaldehyde.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureAfter cooling
  3. customuntil bubbling
  4. customThe insoluble matter was removed by filtration
  5. customThe organic layer was separated
  6. washwashed with a 10% aqueous solution of sodium thiosulfate once
  7. dry with materiala saturated aqueous solution of sodium chloride twice, and dried
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e5ee7ab91d0043e3b3ca6ba6d2a5da47
Source dataset
uspto-grants-1990_03
Patent number
US04912101

Reaction notes

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