反应 #64906

反应方程式

water

8-azaphenanthrene-1,10-dicarboxylic anhydride

sodium nitrate

→

nitro

收率 66.0%

3-Nitro-8-azaphenanthrene-1,10-dicarboxylic Anhydride

收率 66.0%

溶剂

sulfuric acid

反应条件

后处理

1. 1
   洗涤rinsing the residue from the reaction flask with water (4×25 mL)
2. 2
   workup.ADDITIONwas added as a buffer
3. 3
   其他The precipitated solid was collected on a frit
4. 4
   其他dried
5. 5
   温度The crude material was heated
6. 6
   温度at reflux in acetic acid (70 mL)
7. 7
   其他The brown solid was collected on a frit
8. 8
   洗涤washed with acetic acid (20 mL)
9. 9
   其他dried

实验过程

As above for example 2, part A, 8-azaphenanthrene-1,10-dicarboxylic anhydride (7.62 g, 30.6 mmol) was nitrated in concentrated sulfuric acid (30 mL) at 110° C. by the addition of sodium nitrate (6.50 g, 76.5 mmol) in five portions over 31 h. The acid solution was poured into water (300 mL), rinsing the residue from the reaction flask with water (4×25 mL). The aqueous suspension was neutralized to about pH 4 with concentrated sodium hydroxide solution and sodium acetate (5 g) was added as a buffer. The precipitated solid was collected on a frit and dried. The crude material was heated at reflux in acetic acid (70 mL) and acetic anhydride (10 mL) for 4 h and the suspension was cooled to room temperature. The brown solid was collected on a frit, washed with acetic acid (20 mL), and dried to give 5.94 g (66%) of the nitro compound: mp >300° C.; 1H NMR (CDCl3, 300 MHz) δ 7.97 (dd, 1H, J=9.0, 4.5 Hz), 9.16 (d, 1H, J=9.0 Hz), 9.33 (d, 1H, J=4.5 Hz), 9.42 (s, 1H), 9.48 (d, 1H, J=1.5 Hz), 9.87 (d, 1H, J=1.5 Hz); MS (CI, CH4) m/e (%) 295 (M+H+, 100), 250 (4), 121 (6), 103 (4), 93 (19).

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