5-(Aminomethyl)-2-chloropyridine → 1-[2-(6-Chloro-3-pyridinyl)-5-methyl-1H-imidazol-4-yl]ethanone

HRID 615328Notes

Reaction equation

HRID 615328 reaction equation
[CH3:1][C:2](=O)[C:3](=[N:7]O)[C:4](=[O:6])[CH3:5].[Cl:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][CH:12]=1>C(#N)C>[Cl:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[NH:18][C:2]([CH3:1])=[C:3]([C:4](=[O:6])[CH3:5])[N:7]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 178468373HCID 178468373, compound

Product 1

HCID 133879401-[2-(6-Chloro-3-pyridinyl)-5-methyl-1H-imidazol-4-yl]ethanoneYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 4.5 g (0.035 mole) of 2,3,4-pentanetrione 3-oxime and 5.3 g (0.037 mole) of 6-chloro-3-pyridylmethylamine in 100 ml of acetonitrile was stirred at the reflux temperature for 18 hours. The reacted mixture was cooled at -10° C. with formation of a precipitate. The precipitate was washed, dried and recrystallized as for Example 24 to give 2.6 g of the desired product as a pale yellow solid, mp 239°-240° C.

Workup

  1. washThe precipitate was washed
  2. customdried
  3. customrecrystallized as for Example 24

Sources & evidence

ORD record
ord-64e92dd11e624b9c80162ac9dd020b1c
Source dataset
uspto-grants-1985_02
Patent number
US04499097

Reaction notes

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