Nitric Acid → 2,3,8,9-Tetramethoxybenzo[i]phenanthridine

HRID 369758

반응식

HRID 369758 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[C:6]([N+:11]([O-])=O)=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][O:16][C:17]1[CH:18]=[C:19](Br)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].[N+]([O-])(O)=O>C(O)(=O)C>[CH3:15][O:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]2[C:8]3[CH:7]=[N:11][C:6]4[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=4[C:3]=3[CH:4]=[CH:5][C:19]=2[CH:18]=1

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 1709684-Bromo-5-nitroveratrole2회

생성물 1

HCID 98847232,3,8,9-Tetramethoxybenzo[i]phenanthridine수율 92%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
10 °C

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.

후처리

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

출처 및 근거

ORD 기록
ord-c1ca8439c99c47b08db926ebbb9216b9
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140328

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