반응 #64906

반응 방정식

water

8-azaphenanthrene-1,10-dicarboxylic anhydride

sodium nitrate

→

nitro

수율 66.0%

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

수율 66.0%

용매

sulfuric acid

반응 조건

후처리

1. 1
   세척rinsing the residue from the reaction flask with water (4×25 mL)
2. 2
   workup.ADDITIONwas added as a buffer
3. 3
   기타The precipitated solid was collected on a frit
4. 4
   기타dried
5. 5
   온도The crude material was heated
6. 6
   온도at reflux in acetic acid (70 mL)
7. 7
   기타The brown solid was collected on a frit
8. 8
   세척washed with acetic acid (20 mL)
9. 9
   기타dried

실험 절차

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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