반응 #78469

반응 방정식

imidazolide

methyl 5-amino-6-methylaminonicotinate

3-(4-cyanophenyl)propionic acid

→

crude product

Methyl 5-[2-(4-cyanophenyl)ethylcarbonylamino]-6-methylaminonicotinate

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도heated for 3 hours to 100° C
2. 2
   기타After the removal of the solvent in vacuo

실험 절차

A solution of 2.6 g (15 mmol) of 3-(4-cyanophenyl)propionic acid in 25 mL of absolute tetrahydrofuran was mixed with 2.4 g (15 mmol) of N,N′-carbonyldiimidazole and stirred for 20 minutes at room temperature. Then the imidazolide was mixed with a solution of 2.3 g (13 mmol) of methyl 5-amino-6-methylaminonicotinate in 25 mL of dimethyfformamide and heated for 3 hours to 100° C. After the removal of the solvent in vacuo, the crude product obtained was taken up in ethyl acetate, the organic phase was washed with water and after drying over sodium sulfate it was again freed from solvent. The residue obtained was purified by flash chromatography (silica gel; gradient: dichloromethane to dichloromethane/ethanol=19:1). Yield: 2.1 g (50% of theory) of beige solid; Rf value: 0.54 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

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