Dichloromethane → N-(2-chloropyridin-3-yl)acetamide

HRID 876802Notes

Reaction equation

HRID 876802 reaction equation
Cl[C:2]1[C:3](N)=[N:4]C=[CH:6][CH:7]=1.CC[N:11](CC)CC.[C:16](Cl)(=[O:18])[CH3:17].C([O-])(O)=O.[Na+].[CH2:25]([Cl:27])Cl>>[Cl:27][C:25]1[C:6]([NH:11][C:16](=[O:18])[CH3:17])=[CH:7][CH:2]=[CH:3][N:4]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 6932672-Amino-3-chloropyridine

Product 1

HCID 4338791N-(2-chloropyridin-3-yl)acetamide

Procedure

To a mixture of 3-chloropyridin-2-amine (S-1) (12.8 g, 100 mmol) and Et3N (3 mL) in dried DCM (50 mL) was added acetyl chloride (8 mL) dropwise. The reaction was stirred at room temperature overnight, then adjusted to pH about 7 with an aqueous NaHCO3 solution, and extracted with DCM. The organic layer was washed with water, dried over Na2SO4, and concentrated to afford the title compound (17.1 g). MS (m/z): 171.6 (M+1)+.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-182ef1e3c46e4fddbaf15f7824feaff3
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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