Water → HCID 70081578, compound

HRID 461339Notes

Reaction equation

HRID 461339 reaction equation
[CH2:1]([N:3]([CH2:6]C)CC)[CH3:2].[CH2:8]([C:15]1[C:20]([NH2:21])=CC=CN=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[CH2:23][C:24]([Cl:26])=O.[OH2:27]>C1C=CC=CC=1>[CH2:8]([CH2:15][C:20]([NH:21][C:6]1[C:24]([Cl:26])=[CH:23][CH:2]=[CH:1][N:3]=1)=[O:27])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 189526852-Benzylpyridin-3-amine

Product 1

HCID 70081578HCID 70081578, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

3.4 ml tri-ethylamine is added to a solution of 4.5 g (0.025 mol) 2-benzyl-3-aminopyridine in 25 ml dry benzene. A solution of 2 ml chloro-acetyl chloride in 40 ml dry benzene is then added with stirring to this solution at a temperature of 5°-10° C. The mixture is stirred for 30 minutes at room temperature and a precipitate forms. This precipitate is redissolved by addition of 50 ml water and 50 ml benzene to the mixture. The organic phase is subsequently separated off, dried, and evaporated to dryness. The residue, a white solid, is recrystallized from a little benzene, giving 5.78 g (92%) 2-benzyl-3-chloro-acetamidopyridine of melting point 145°-147° C.

Workup

  1. stirringThe mixture is stirred for 30 minutes at room temperature
  2. customThe organic phase is subsequently separated off
  3. customdried
  4. customevaporated to dryness
  5. customThe residue, a white solid, is recrystallized from a little benzene

Sources & evidence

ORD record
ord-a1c92ce32d7b47cfb539f427963d5278
Source dataset
uspto-grants-1977_12
Patent number
US04062848

Reaction notes

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