Acetyl chloride → N-(5,6-dichloropyridin-3-yl)acetamide

HRID 1479556Notes

Reaction equation

HRID 1479556 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[N:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:17](=[O:19])[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 145952195-Amino-2,3-dichloropyridine

Product 1

HCID 86652352N-(5,6-dichloropyridin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5,6-dichloropyridin-3-amine (commercially available) and triethyl amine (3 eq) in CH2Cl2 (0.2 M) at 0° C. was added acetyl chloride (2 eq). After stirring at room temperature overnight the reaction mixture was concentrated under vacuum and the resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes) to afford N-(5,6-dichloropyridin-3-yl)acetamide.

Workup

  1. concentrationwas concentrated under vacuum
  2. customthe resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-70c462645a8a4d75bb5b8101918567f6
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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