反応 #158319

反応方程式

methyl 4-[formyl(2-oxopropyl)amino]-3-methoxybenzoate

ammonium acetate

ethyl acetate

sodium hydrogen carbonate

→

title compound

収率 52.9%

methyl 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoate

収率 52.9%

溶媒

acetic acid

反応条件

後処理

1. 1
   workup.ADDITIONwere added under ice-
2. 2
   温度cooling
3. 3
   その他the organic layer was separated
4. 4
   workup.ADDITIONTo the aqueous layer was added ethyl acetate
5. 5
   その他the organic layer was separated
6. 6
   洗浄washed with saturated brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   その他the solvent was evaporated under reduced pressure
9. 9
   その他The residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane)

実験手順

A mixture of methyl 4-[formyl(2-oxopropyl)amino]-3-methoxybenzoate (32.6 g) and ammonium acetate (47.5 g) in acetic acid (65.6 mL) was stirred at 140° C. for 1 hr. After completion of the reaction, ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added under ice-cooling, and the organic layer was separated. To the aqueous layer was added ethyl acetate, and the organic layer was separated. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane) to give the title compound (16.0 g).

出典