تفاعل #45243

معادلة التفاعل

3-hydrazino-benzoic acid hydrochloride

4,4-dimethyl-3-oxo-pentanenitrile

ethanol

→

3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester

المردود 40.0%

3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid

المردود 36.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةto reflux overnight
3. 3
   أخرىThe reaction solution was evaporated under reduced pressure
4. 4
   أخرىThe residue was purified by column chromatography

الإجراء التجريبي

A mixture of 3-hydrazino-benzoic acid hydrochloride (200 g, 1.06 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (146 g, 1.167 mol) in ethanol (2 L) was heated to reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester (116 g, 40%) as a white solid together with 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid (93 g, 36%). 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid and ethyl ester: 1H NMR (DMSO-d6): 8.09 (s, 1H), 8.05 (brd, J=8.0 Hz, 1H), 7.87 (br d, J=8.0 Hz, 1H), 7.71 (t, J=8.0 Hz, 1H), 5.64 (s, 1H), 4.35 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H), 1.28 (s, 9H).

المصدر