Hydrazine hydrate (1:1) → Methyl 2-[4-(aminomethyl)phenyl]benzoate

HRID 1646922

Reaktionsgleichung

Reaktionsgleichung von HRID 1646922
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)=[CH:13][CH:12]=1)([O:3][CH3:4])=[O:2].O.NN>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:27][CH:28]=1)([O:3][CH3:4])=[O:2]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 19794415N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

Produkt 1

HCID 1393434Methyl 2-[4-(aminomethyl)phenyl]benzoateAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Compound (f) of Example 6 (3.85 g, 0.01 mole) is dissolved in 100 mL of absolute ethanol with warming. Hydrazine hydrate (7.5 mL) is added at once. The solution is heated to reflux for 10 minutes and the reaction mixture sets up. The mixture is cooled to room temperature and filtered. The precipitate is washed with excess hot ethanol. The ethanol fraction is rotovapped to a pale yellow oil. Chromatography on silica gel using methylene chloride/25% methanol as the mobile phase yields 1.6 g (66%) of a pale yellow oil. 1H NMR (CDCl3) 7.83 (1H, d, J=7 Hz); 7.6-7.2 (7H, m); 3.92 (2H, s); 3.66 (3H, s); 2.16 (2H, bs). Mass Spec. (DCI) m/z 242 (M+H). Analysis-calc'd for C15H15NO2.H2O: C, 71.97; H, 6.44; N, 5.60; found: C, 71.60; H, 6.27; N, 5.70.

Aufarbeitung

  1. temperaturewith warming
  2. temperatureThe solution is heated
  3. temperatureto reflux for 10 minutes
  4. filtrationfiltered
  5. washThe precipitate is washed with excess hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b05d08e10ace4944bcf7e1059762d3a6
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182288

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