Potassium Iodide → HCID 23294826, compound

HRID 1004315Notes

Reaction equation

HRID 1004315 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18]Cl)[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:18][C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 72132,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 23294826HCID 23294826, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4-dihydroxybenzaldehyde (25 g), 3-picolyl chloride hydrochloride (38.2 g), potassium carbonate (91 g), potassium iodide (0.5 g) and tetra-n-butylammonium bromide (0.5 g) in methyl ethyl ketone (1000 ml) was heated at reflux for 4 hours. The reaction mixture was filtered and evaporated. The residue was partitioned between ethyl acetate and dilute acetic acid. The organic phase was washed with water, dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica eluting initially with a mixture of pentane and ethyl acetate (3:1, v/v) then with a mixture of pentane and ethyl acetate (1:1, v/v) and finally with a mixture of pentane and ethyl acetate (85:15, v/v). Fractions homogenous in the required product were combined and evaporated affording the title compound (5 g) as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. filtrationThe reaction mixture was filtered
  4. customevaporated
  5. customThe residue was partitioned between ethyl acetate and dilute acetic acid
  6. washThe organic phase was washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica eluting initially with a mixture of pentane and ethyl acetate (3:1
  10. additionv/v) then with a mixture of pentane and ethyl acetate (1:1
  11. additionv/v) and finally with a mixture of pentane and ethyl acetate (85:15
  12. customevaporated

Sources & evidence

ORD record
ord-0f7de0296e9349059415e6e77d958eea
Source dataset
uspto-grants-2000_04
Patent number
US06048893

Reaction notes

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