Ammonium Hydroxide → o-Desmethyl metoclopramide

HRID 1086027Notes

Reaction equation

HRID 1086027 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 9817332o-Desmethyl metoclopramide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2256625098a64aa0bc0bd9da245f8ea7
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

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