methyl 2-aminobutanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An acetonitrile solution (15 ml) of 2-oximino-1-phenyl-1,3-butanedione (1.38 g, 7.22 mmoles) and methyl 2-aminobutyrate (0.85 ml, 7.22 mmol) was refluxed under nitrogen for 26.4 h. After concentrating the cooled reaction mixture, the residue was dissolved in 10 ml of ethanol and 20 ml of 10% aqueous sodium hydroxide. This mixture was refluxed 4.9 h, cooled, then extracted with ethyl acetate. Removal of the solvent in vacuo gave 0.65 g (42% yield) of 5-benzoyl-2-ethyl-4-methylimidazole and 5-acetyl-2-ethyl-4-phenylimidazole (86:14 respectively). After concentrating the cooled reaction mixture This mixture was refluxed 4.9 h cooled extracted with ethyl acetate Removal of the solvent in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4.99 g (0.039 moles) of 3-oximino-2,4-pentanedione dissolved in acetonitrile (40 ml) was added 4.59 ml (0.039 moles) of methyl 2-aminobutyrate. After stirring for two hours at room temperature, then at reflux for 2.5 h, the reaction mixture was cooled and treated with 15 ml of ethanol and 15 ml of 10% aqueous sodium hydroxide. The resulting mixture was refluxed for 3.8 h, cooled, then extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, then concentrated in vacuo to give 0.024 moles (62% yield) of 5-acetyl-2-ethyl-4-methylimidazole. at reflux for 2.5 h the reaction mixture was cooled The resulting mixture was refluxed for 3.8 h cooled extracted with ethyl acetate The combined organic extracts were dried over anhydrous sodium sulfate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4.99 g (0.039 moles) of 3-oximino-2,4-pentanedione dissolved in acetonitrile (40 ml) was added 4.59 ml (0.039 moles) of methyl 2-aminobutyrate. After stirring for two hours at room temperature, then at reflux for 2.5 h, the reaction mixture was cooled and treated with 15 ml of ethanol and 15 ml of 10% aqueous sodium hydroxide. The resulting mixture was refluxed for 3.8 h, cooled, then extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, then concentrated in vacuo to give 0.024 moles (62% yield) of 5-acetyl-2-ethyl-4-methylimidazole. at reflux for 2.5 h the reaction mixture was cooled The resulting mixture was refluxed for 3.8 h cooled extracted with ethyl acetate The combined organic extracts were dried over anhydrous sodium sulfate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: