2-Amino-4-methylpyridine → 2-Chloro-N-(4-methylpyridin-2-yl)acetamide

HRID 1973227Notes

Reaction equation

HRID 1973227 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>CCOCC>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:18](=[O:19])[CH2:17][Cl:16])[CH:7]=1

Participants

5

Reactant 3

HCID 15332-Amino-4-methylpyridineHCID 6577Chloroacetyl chlorideHCID 8471Triethylamine

Product 1

HCID 27767972-Chloro-N-(4-methylpyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-amino-4-methylpyridine (10.8 grams) in ether (150 ml), and triethylamine (10 grams) are placed in a reaction flask equipped with stirrer, thermometer and addition funnel. The reaction mixture is cooled to a temperature of about 0° C and chloroacetyl chloride (11.3 grams) dissolved in ether (30 ml) is slowly added thereto resulting in the formation of a precipitate. Stirring is continued for a period of about 1 hour. After this time the reaction mixture is filtered to recover the precipitate that has formed. The precipitate is washed with aqueous potassium carbonate and with water. The washed precipitate is then dried to yield the desired product N-(4-methyl-2-pyridyl)-α-chloroacetamide.

Workup

  1. customequipped with stirrer
  2. additionthermometer and addition funnel
  3. additionis slowly added
  4. customthereto resulting in the formation of a precipitate
  5. filtrationAfter this time the reaction mixture is filtered
  6. customto recover the precipitate that
  7. customhas formed
  8. washThe precipitate is washed with aqueous potassium carbonate and with water
  9. customThe washed precipitate is then dried

Sources & evidence

ORD record
ord-4ccc0c77a17f40e98b2fc8f126e23ccc
Source dataset
uspto-grants-1976_12
Patent number
US03996352

Reaction notes

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