3-(Chloromethyl)pyridine hydrochloride → HCID 23076389, compound

HRID 2221559Notes

Reaction equation

HRID 2221559 reaction equation
[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.Cl.Cl[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[H-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][O:1][C:2]2[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:3]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178469940HCID 178469940, compound

Product 1

HCID 23076389HCID 23076389, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 3-hydroxy-1H-pyrazole-4-carboxylate (1.06 g), 3-chloromethylpyridine hydrochloride (2.79 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (60% in oil, 1.36 g) at 0° C. The mixture was stirred at room temperature for 15 hrs. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, from a fraction eluted with ethyl acetate-methanol (10:1, v/v), ethyl 3-(pyridin-3-ylmethoxy)-1-(pyridin-3-ylmethyl)-1H-pyrazole-4-carboxylate as colorless crystals (1.23 g, yield 53%). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 120-121° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-methanol (10:1

Sources & evidence

ORD record
ord-9afac6d1764440aeb91fd4361811d5aa
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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