Chloroacetyl chloride → 2-chloro-N-(pyridin-3-yl)acetamide

HRID 2192341Notes

Reaction equation

HRID 2192341 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Cl:10][CH2:11][C:12](Cl)=[O:13]>O>[Cl:10][CH2:11][C:12]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:13]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 100093-AminopyridineHCID 14798Sodium Hydroxide

Product 1

HCID 50864572-chloro-N-(pyridin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-aminopyridine (350 mg) and sodium hydroxide (0.6 g) were dissolved in water (8 mL) and the reaction mixture was cooled in an ice bath. Chloroacetyl chloride (1.19 mL) was added dropwise and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was extracted with dichloromethane and organic layer was concentrated and purified by column chromatography, eluting with 0-60% ethyl acetate/cyclohexane to give the title compound (0.10 g) as a white solid.

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. extractionThe reaction mixture was extracted with dichloromethane and organic layer
  3. concentrationwas concentrated
  4. custompurified by column chromatography
  5. washeluting with 0-60% ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-f9567ad326cf414facc507cbeb51e85e
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

Loading…