Ammonium Hydroxide → o-Desmethyl metoclopramide

HRID 620246

Reaktionsgleichung

Reaktionsgleichung von HRID 620246
[OH-].[NH4+].Cl.[NH2:4][C:5]1[C:20]([Cl:21])=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:10])=[C:7]([OH:22])[CH:6]=1>O>[NH2:4][C:5]1[C:20]([Cl:21])=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[O:10])=[C:7]([OH:22])[CH:6]=1

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Produkt 1

HCID 9817332o-Desmethyl metoclopramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To stirred concentrated ammonium hydroxide (6 ml) was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (3.0 grams, 0.0093 mole) and the mixture stirred an additional five minutes followed by the addition of three to four ml of water and another five minute stirring. After filtration the solid was washed two times with three ml of water each time to give, after drying, 2.37 g of the title compound, mp 134°-136° C. NMR spectrum (90 MHz) in CDCl3 gave the following resonances δ: 7.26 (s, 1H); 6.90 (s, 1H); 6.14 (s, 1H); 4.39 (s, 2H); 3.40 (s, 2H); 2.60 (multiplet, 6H); 1.06 (t, 6H).

Aufarbeitung

  1. stirringstirring
  2. filtrationAfter filtration the solid
  3. washwas washed two times with three ml of water each time
  4. customto give
  5. customafter drying
  6. customNMR spectrum (90 MHz) in CDCl3 gave the following resonances

Quellen und Nachweise

ORD-Eintrag
ord-4f0df26f1e5449f98bd2639c6581b88b
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04820715

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