Dichloromethane → 2-Chloro-N-pyridin-2-yl-acetamide

HRID 1979979Notes

Reaction equation

HRID 1979979 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(Cl)Cl.[Cl:11][CH2:12][C:13](Cl)=[O:14]>O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:13](=[O:14])[CH2:12][Cl:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 104392-Aminopyridine

Product 1

HCID 2894352-Chloro-N-pyridin-2-yl-acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 9.42 g. (0.1 mole) of 2-aminopyridine in 50 ml. of methylene chloride was added dropwise 4.0 ml. (0.05 mole) of chloroacetyl chloride in 20 ml. of the same solvent, keeping the reaction temperature at -20° to -10° C. for one hour. After stirring at room temperature for 10 hours, 50 ml. of water was added and the organic layer separated. The organic solution was washed with water and a brine solution and was dried over magnesium sulfate. Removal of the solvent in vacuo gave 6.64 g. (78%), m.p. 114°-117° C., of the desired product.

Workup

  1. customat -20° to -10° C.
  2. customfor one hour
  3. customthe organic layer separated
  4. washThe organic solution was washed with water
  5. dry with materiala brine solution and was dried over magnesium sulfate
  6. customRemoval of the solvent in vacuo
  7. customgave 6.64 g

Sources & evidence

ORD record
ord-255fd9d884424a6ba1bc1101d76dd969
Source dataset
uspto-grants-1984_11
Patent number
US04483982

Reaction notes

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