Acetonitrile → 5-Methyl-2-pyridin-3-YL-3H-imidazole-4-carboxylic acid ethyl ester

HRID 1252368Notes

Reaction equation

HRID 1252368 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[C:5](=O)[C:6](=O)[CH3:7])[CH3:2].[NH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(#[N:21])C>>[CH3:7][C:6]1[NH:21][C:12]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[N:11][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:10]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 310183-PyridinemethanamineHCID 12260829Ethyl 2,3-dioxobutanoate

Product 1

HCID 534358745-Methyl-2-pyridin-3-YL-3H-imidazole-4-carboxylic acid ethyl ester

Conditions

Temperature
-10 °C

Procedure

A solution of 16 g of 2,3-dioxobutyric acid ethyl ester, (Z)-2-oxime, 12 g of 3-aminomethylpyridine and 100 ml of acetonitrile was stirred at reflux for 4 hours, then clarified while hot and the filtrate cooled at -10° C. The resulting precipitate was collected, washed with acetonitrile, air dried and recrystallized from acetonitrile at -10° C., giving 4.8 g of 5-methyl-2-(3-pyridinyl)-1H-imidazole-4-carboxylic acid, ethyl ester.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe resulting precipitate was collected
  3. washwashed with acetonitrile, air
  4. customdried
  5. customrecrystallized from acetonitrile at -10° C.

Sources & evidence

ORD record
ord-f1e427162e704b248f2999ec89e0e348
Source dataset
uspto-grants-1988_05
Patent number
US04743586

Reaction notes

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