반응 #456940

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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

수율 92.0%

용매

acetic acid

—

ice

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후처리

1. 1
   추출The resulting mixture was extracted thrice with 200 mL portions of ether
2. 2
   기타The combined organic phase was dried
3. 3
   기타evaporated in vacuo
4. 4
   기타The crude product was recrystallized from ethanol
5. 5
   기타to give bright yellow needle

실험 절차

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.

출처