3-Nitrophthalic acid → 3-Aminophthalic acid

HRID 32779

Reaktionsgleichung

Reaktionsgleichung von HRID 32779
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14]

Komponenten

5

Edukt 2

HCID 690433-Nitrophthalic acidHCID 178418361HCID 178418361, Verbindung3×

Produkt 1

HCID 794903-Aminophthalic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

10% Pd/C (2.5 g), 3-nitrophthalic acid (75.0 g, 355 mmol) and ethanol (1.5 L) were charged to a 2.5 L Parr hydrogenator, under a nitrogen atmosphere. Hydrogen was charged to the reaction vessel for up to 55 psi. The mixture was shaken for 13 hours, maintaining hydrogen pressure between 50 and 55 psi. Hydrogen was released and the mixture was purged with nitrogen 3 times. The suspension was filtered through a celite bed and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solid was reslurried in ether and isolated by vacuum filtration. The solid was dried in vacua to a constant weight, affording 54 g (84% yield) of 3-aminopthalic acid as a yellow product. 1H-NMR (DMSO-d6) δ: 3.17 (s, 2H), 6.67 (d, 1H), 6.82 (d, 1H), 7.17 (t, 1H), 8-10 (brs, 2H). 13C-NMR DMSO-d6)δ: 112.00, 115.32, 118.20, 131.28, 135.86, 148.82, 169.15, 170.09.

Aufarbeitung

  1. customthe mixture was purged with nitrogen 3 times
  2. filtrationThe suspension was filtered through a celite bed
  3. washrinsed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customisolated by vacuum filtration
  6. customThe solid was dried in vacua to a constant weight

Quellen und Nachweise

ORD-Eintrag
ord-6d65cc5485e74a759a1e487207bb97d3
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427638B2

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