Potassium Hydroxide → HCID 18182261, compound

HRID 1359261Notes

Reaction equation

HRID 1359261 reaction equation
[Br:1]Br.[Br-].[K+].[CH2:5]([C:12]1[CH:17]=[CH:16][N:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[K+].S([O-])([O-])=O.[Na+].[Na+]>[Cl-].C([N+](CC)(CC)CC)C.O>[CH2:5]([C:12]1[C:17]([Br:1])=[CH:16][N:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 253877Potassium Bromide2×HCID 18182389HCID 18182389, compound

Product 1

HCID 18182261HCID 18182261, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 962WaterSolvent2×

Procedure

A mixed solution of 22 ml of bromine, 90 g of potassium bromide and 500 ml of water was added dropwise into a mixture of 73 g of 4-benzyl-2-methoxypyridine, 28 g of potassium hydroxide, 1.7 g of tetraethylammonium chloride, 90 g of potassium bromide and 500 ml of water under stirring in an ice bath. After stirring overnight, sodium sulfite was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 62 g of the target compound.

Workup

  1. stirringAfter stirring overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-b1d12287125d46d1ae2621a89e6b82fe
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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