Sodium Iodide → HCID 20080362, compound

HRID 1653644Notes

Reaction equation

HRID 1653644 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:15]([O:17]C)=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]1(C(Cl)=O)[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)C(C)C)(C)C.[I-].[Na+]>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([C:15]([OH:17])=[O:16])=[N:11][C:12]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 709371-Pyrrolidinecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 22175081Methyl 3-benzyloxypicolinate

Product 1

HCID 20080362HCID 20080362, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.48 g (25 mmol) of methyl 3-benzyloxypicolinate (N-oxide), 6.68 g (50 mmol) of 1-pyrrolidinylcarbonyl chloride, 6.46 g (50 mmol) of N,N-diisopropylethylamine and 7.49 g (50 mmol) of sodium iodide were refluxed under heating for two hours in 120 ml of acetonitrile. The solvent was distilled off, and water was added to the residue. The mixture was extracted with ethyl acetate, washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained mixture was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain the desired product.

Workup

  1. distillationThe solvent was distilled off
  2. additionwater was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe obtained mixture was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-0b3dc2d38db7453d94e1924942a9a06e
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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