Methyl 4-nitrobenzoate → Benzoic acid, 4-nitro-, hydrazide

HRID 1715244

Reaktionsgleichung

Reaktionsgleichung von HRID 1715244
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.[NH2:15][NH2:16]>CCO>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:15][NH2:16])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 12083Methyl 4-nitrobenzoateHCID 24654Hydrazine hydrate (1:1)

Produkt 1

HCID 3693744Benzoic acid, 4-nitro-, hydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl 4-nitrobenzoate (5.42 g; 29.92 mmol; 1 eq.) is dissolved in EtOH (120 ml). Hydrazine hydrate (7.27 ml; 149.60 mmol; 5 eq.) is added and the mixture is stirred 1 hour at rt. It is stirred at 60° C. for 6 hours and rt overnight. The precipitate formed is filtrated and dried under vacuo, affording 4-nitrobenzohydrazide as white-off solid (4.31 g; 79%). 1H NMR (DMSO-d6) δ: 4.63 (s, 2H), 8.03 (d, J=9 Hz, 2H), 8.23 (d, J=9 Hz, 2H), 10.12 (s, 1H). HPLC (method A), Rt: 0.78 min (purity: 100.0%).

Aufarbeitung

  1. stirringIt is stirred at 60° C. for 6 hours and rt overnight
  2. customThe precipitate formed
  3. filtrationis filtrated
  4. customdried under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c8df53604b464aae9d4f28b0d3958dc7
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799814B2

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