Ethanol → 1-(3-Hydroxy-5-aminobenzoyl)-2-benzoylhydrazine

HRID 431388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 431388
C1C2C(=CC=CC=2)C=CC=1C[O:12][C:13]1[CH:14]=[C:15]([CH:28]=[C:29]([N+:31]([O-])=O)[CH:30]=1)[C:16]([NH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17].CCO>[Pd].CN(C=O)C>[OH:12][C:13]1[CH:14]=[C:15]([CH:28]=[C:29]([NH2:31])[CH:30]=1)[C:16]([NH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17]

Komponenten

5

Edukt 2

HCID 702EthanolHCID 187634381-{3-[(2-Naphthyl)methoxy]-5-nitrobenzoyl)-2-benzoylhydrazine

Produkt 1

HCID 187634351-(3-Hydroxy-5-aminobenzoyl)-2-benzoylhydrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-{3-[(2-naphthyl)methoxy]-5-nitrobenzoyl}-2-benzoylhydrazine (0.34 g, 0.77 mmol), Pd/C (10%, 0.35 g), EtOH (10 mL), and DMF (10 mL) was hydrogenated in Parr apparatus (H2 pressure—30 psi) at room temperature for 1.5 h. Catalyst was filtered off, and filtrate concentrated in vacuo to give a slurry of white needles, which were filtered and washed with EtOH (3×25 mL). Yield 0.20 g (96%). 1H NMR (DMSO-d6, 400 MHz), δ: 10.37 (s, 1H); 10.12 (s, 1H); 9.20 (s, 1H); 7.91 (d, J=7.0 Hz, 2H); 7.62-7.48 (m, 3H); 6.54 (s, 1H); 5.46 (s, 1H); 6.19 (s, 1H); 5.18 (br.s, 2H).

Aufarbeitung

  1. filtrationCatalyst was filtered off
  2. concentrationfiltrate concentrated in vacuo
  3. customto give a slurry of white needles, which
  4. filtrationwere filtered
  5. washwashed with EtOH (3×25 mL)

Quellen und Nachweise

ORD-Eintrag
ord-3997371e0938483bb07d70e5bbfe207b
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06656971B2

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