反応 #456940

反応方程式

compound 16

3,4-Dimethoxy-6-nitro-bromobenzene

3,4-Dimethoxy-6-nitro-bromobenzene

3,4-Dimethoxybromobenzene

nitric acid

→

2,3,8,9-Tetramethoxybenzo[i]phenanthridine

収率 92.0%

溶媒

acetic acid

—

ice

反応条件

後処理

1. 1
   抽出The resulting mixture was extracted thrice with 200 mL portions of ether
2. 2
   その他The combined organic phase was dried
3. 3
   その他evaporated in vacuo
4. 4
   その他The crude product was recrystallized from ethanol
5. 5
   その他to give bright yellow needle

実験手順

3,4-Dimethoxy-6-nitro-bromobenzene (16). 3,4-Dimethoxybromobenzene (5 g, 23 mmol) was slowly added to a stirred solution of 35 mL concentrated nitric acid and 105 mL glacial acetic acid maintained at 10° C. The reaction mixture was stirred at 15° C. for 1 h and then diluted with 200 mL ice cold water. The resulting mixture was extracted thrice with 200 mL portions of ether. The combined organic phase was dried and evaporated in vacuo. The crude product was recrystallized from ethanol to give bright yellow needle shaped crystals of compound 16 in 92% yield; mp=122-124° C.; IR (Nujol) 1510, 1312; 1H NMR δ 3.94 (3H, s), 3.97 (3H, s), 7.12 (1H, s), 7.57 (1H, s); 13C NMR δ 56.9, 57.2, 108.0, 109.5, 117.0, 148.7, 153.3; Anal. calcd for C8H8NO4Br: C, 36.72, H, 3.14, N, 5.30; Found: C, 36.70, H, 3.13, N, 5.29.

出典