Reaktion #166189

Reaktionsgleichung

4-amino-2-chloro-3-methyl-benzoic acid methyl ester

isoamylnitrite

→

title compound

Ausbeute 40.5%

4-Chloro-1H-indazole-5-carboxylic acid methyl ester

Ausbeute 40.5%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen heated
2. 2
   Temperaturat reflux for 3 hours
3. 3
   EinengenThe reaction mixture was concentrated in vacuo

Vorschrift

To a solution of 4-amino-2-chloro-3-methyl-benzoic acid methyl ester (5.29 g, 26.5 mmol) in acetic acid (100 mL) was added isoamylnitrite (3.9 mL, 29.2 mmol). The reaction mixture was stirred at room temperature for 30 minutes then heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, gradient 0-100% ethyl acetate in cyclohexane) to yield the title compound as an off-white solid (2.26 g, 40%). 1H NMR (CDCl3, 400 MHz) 3.97 (3H, s), 7.42 (1H, d, J=8.8 Hz), 7.95 (1H, d, J=8.8 Hz), 8.29 (1H, s).

Quelle