Metronidazole → Metronidazole monosuccinate

HRID 1822123Notes

Reaction equation

HRID 1822123 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[OH-].[Na+].[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1>CO>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][C:15]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:21])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 4173MetronidazoleHCID 7922Succinic anhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 83212Metronidazole monosuccinateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
8 °C

Procedure

In a 100 mL reactor with 10 mL of methanol at a temperature about 60° C., add 0.315 g of metronidazole, 2.0 mL of NaOH 1N, 0.2 g of succinic anhydride and keep the reaction medium under stirring and heating for about 2 hours. Cool the reaction medium to a temperature around 8° C. and allow it to stand for 12 hours. The reaction medium is filtered and the solvent is evaporated to dryness yielding 0.47 g of metronidazole monosuccinate. (Yield=94%)

Workup

  1. temperatureheating for about 2 hours
  2. filtrationThe reaction medium is filtered
  3. customthe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-d78e9f4686f14ff79a66c40b9f5dda57
Source dataset
uspto-grants-2009_10
Patent number
US07608724B2

Reaction notes

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