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

HRID 354640

Reaction equation

HRID 354640 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-c8118f53ef5d431aaa4f72d8f69651ac
Source dataset
uspto-grants-1983_03
Patent number
US04376204

Linked notes

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