تفاعل #86437

معادلة التفاعل

4-amino-3-nitro-phenol

(2-chloro-ethyl)-dimethyl-amine hydrogen chloride

Cs2CO3

NaI

→

title compound

المردود 45.0%

4-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine

المردود 45.0%

المذيبات

butanone

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe solution was filtered through Celite®
2. 2
   غسيلwashed with acetone
3. 3
   أخرىThe solution was evaporated with silica gel
4. 4
   أخرىpurified by flash chromatography on silica

الإجراء التجريبي

To a stirred solution of 4-amino-3-nitro-phenol (1.54 g, 10 mmol) and (2-chloro-ethyl)-dimethyl-amine hydrogen chloride (1.43 g, 10 mmol) in butanone (40 mL) was added Cs2CO3 (10 g, 30 mmol) and NaI (150 g, 1 mmol). The solution was slowly heated to 80° C. over one hour. Then the solution was stirred at 80° C. for 2 hours. The solution was filtered through Celite® and washed with acetone. The solution was evaporated with silica gel and purified by flash chromatography on silica to afford the title compound (1.0 g, yield: 45%) as a brown solid. 1H-NMR (300 MHz, DMSO-d6) δ 7.38 (d, 1H), 7.24 (s, 2H), 7.16 (dd, 2H), 6.99 (d, 1H), 3.98 (t, 214), 2.58 (t, 2H), 2.20 (s, 6H); MS (ESI) 226 [M+H]+.

المصدر