Potassium Iodide → HCID 10656935, compound

HRID 1955157Notes

Reaction equation

HRID 1955157 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[N:19]1[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][CH:20]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:25][C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 745714-(Chloromethyl)pyridineHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 10656935HCID 10656935, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-fluoro-4-hydroxybenzonitrile (10.96 g; S. M. Kelly, Helv. Chim. Acta 1984, volume 67, p1572-1579), potassium carbonate (53.2 g), potassium iodide (6.64 g), tetra-n-butylammonium bromide (0.4 g) and 4-picolyl chloride (14.4 g) in methyl ethyl ketone (600 ml) was stirred at reflux for 3 hours. The reaction mixture was filtered and the insoluble material washed with methyl ethyl ketone. The combined filtrate plus washings were evaporated and the residue partitioned between ethyl acetate (300 ml) and water (150 ml). The aqueous phase was extracted twice with ethyl acetate (100 ml) and the combined ethyl acetate solutions washed with brine (100 ml), dried over magnesium sulphate and evaporated. The residue was recrystallized from a mixture of ethyl acetate and pentane to give the title compound (11.5 g) as a plum coloured solid, m.p. 132-133° C.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe insoluble material washed with methyl ethyl ketone
  4. customThe combined filtrate plus washings were evaporated
  5. customthe residue partitioned between ethyl acetate (300 ml) and water (150 ml)
  6. extractionThe aqueous phase was extracted twice with ethyl acetate (100 ml)
  7. washthe combined ethyl acetate solutions washed with brine (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue was recrystallized from a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-eb726633d907429ab52df7d202f7f682
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

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