Acetyl chloride → N-(2-chloropyridin-3-yl)acetamide

HRID 2259519Notes

Reaction equation

HRID 2259519 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[C:15](Cl)(=[O:17])[CH3:16].[NH4+].[Cl-]>C1COCC1>[C:15]([NH:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 4338791N-(2-chloropyridin-3-yl)acetamideYield 105.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-3-pyridinamine (14.9 g, 116 mmol) in 300 mL of THF was added K2CO3 (32 g, 232 mmol) and acetyl chloride (12 mL, 169 mmol) and the mixture was stirred at room temperature overnight. Saturated NH4Cl was added and the product was extracted in EtOAc, dried over Na2SO4, and filtered through silica to yield 20.81 g of the title amide.

Workup

  1. extractionthe product was extracted in EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered through silica

Sources & evidence

ORD record
ord-58566421fd714bcbad34d4c21fc54a0a
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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