Reaktion #156537

Reaktionsgleichung

4-amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acid

EDCI hydrochloride

HOBt

N1,N1-dimethylethane-1,2-diamine

→

designed compound

Ausbeute 90.0%

5-Amino-2-(2-(dimethylamino)ethyl)-4-methyl-6-nitroisoindoline-1,3-dione

Ausbeute 90.0%

Lösungsmittel

THF

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturat reflux for 14 h under an argon atmosphere
3. 3
   SonstigeProduct was purified by a silica gel column

Vorschrift

To a solution of 4-amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acid (0.43 g, 1.69 mmol), EDCI hydrochloride (0.36 g, 1.86 mmol), and HOBt (0.23 g, 1.69 mmol) in 22 mL of anhydrous THF was added 1.18 mL of triethylamine and stirred for 10 min at rt under an argon atmosphere. N1,N1-dimethylethane-1,2-diamine (0.16 g, 1.86 mmol) was added into above mixture and the reaction mixture was heated at reflux for 14 h under an argon atmosphere. Product was purified by a silica gel column using methylene chloride and methanol (9:1 v/v) as eluent to afford 0.44 g (90%) of the designed compound as yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.21 (s, ArH), 8.12 (br s, 2H, NH2), 3.64 (t, J=6.5 Hz, 2H, CH2), 2.57 (s, 3H, CH3), 2.45 (t, J=6.5 Hz, 2H, CH2), 2.15 (S, 6H, 2×CH3); Mass (ESI, positive) m/z 293.0 [M+H]+.

Quelle