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

HRID 369758

反応式

HRID 369758 の反応式
[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

参加物

5

反応物 3

HCID 944Nitric AcidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 1709684-Bromo-5-nitroveratrole2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
10 °C

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.

後処理

  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

出典と根拠

ORDレコード
ord-c1ca8439c99c47b08db926ebbb9216b9
出典データセット
uspto-grants-2000_10
特許番号
US06140328

関連ノート

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