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

HRID 36628

Reaktionsgleichung

Reaktionsgleichung von HRID 36628
[C:1]12[C:18](=[O:19])[O:17][C:15](=[O:16])[C:13]3[C:14]1=[C:5]([C:6]1[C:11]([CH:12]=3)=[N:10][CH:9]=[CH:8][CH:7]=1)[CH:4]=[CH:3][CH:2]=2.[N+:20]([O-])([O-:22])=[O:21].[Na+].O>S(=O)(=O)(O)O>[N+:20]([C:3]1[CH:2]=[C:1]2[C:18](=[O:19])[O:17][C:15](=[O:16])[C:13]3=[CH:12][C:11]4[C:6]([C:5]([CH:4]=1)=[C:14]23)=[CH:7][CH:8]=[CH:9][N:10]=4)([O-:22])=[O:21]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24268Sodium NitrateHCID 107769938-Azaphenanthrene-1,10-dicarboxylic anhydride

Produkt 1

HCID 152918253-Nitro-8-azaphenanthrene-1,10-dicarboxylic AnhydrideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. washrinsing the residue from the reaction flask with water (4×25 mL)
  2. additionwas added as a buffer
  3. customThe precipitated solid was collected on a frit
  4. customdried
  5. temperatureThe crude material was heated
  6. temperatureat reflux in acetic acid (70 mL)
  7. customThe brown solid was collected on a frit
  8. washwashed with acetic acid (20 mL)
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a36c28d73e4044549adc5456a0b40a19
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416089

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