Water → HCID 67074130, compound

HRID 2359105Notes

Reaction equation

HRID 2359105 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.N1C=CC=CC=1.[CH3:15][O:16][CH2:17][C:18](Cl)=[O:19].O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:18](=[O:19])[CH2:17][O:16][CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 67074130HCID 67074130, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-aminopyridine (173 mmol) and pyridine (347 mol) in 250 mL dichloromethane was added dropwise 2-methoxyacetyl chloride (208 mmol). The reaction mixture was stirred at room temperature for 3 h. Water was added and the reaction mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was washed with hexane to afford 35.0 g of N-(4-bromopyridin-2-yl)-2-methoxyacetamide (82% yield).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-4a84648c73ab478d92bdefee6b4f092d
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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