Lithium Hydroxide → N-Methyl-5-(1-methyl-1H-imidazol-2-yl)-N-propyl-isophthalamic acid

HRID 732549Notes

Reaction equation

HRID 732549 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:16]=[C:15]([C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Li+].[OH-].[Na+]>CO>[CH3:13][N:9]([CH2:10][CH2:11][CH3:12])[C:7](=[O:8])[C:6]1[CH:5]=[C:4]([CH:16]=[C:15]([C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)[CH:14]=1)[C:3]([OH:23])=[O:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 68814383N-Methyl-5-(1-methyl-1H-imidazol-2-yl)-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 68814352N-Methyl-5-(1-methyl-1H-imidazol-2-yl)-N-propyl-isophthalamic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve N-methyl-5-(1-methyl-1H-imidazol-2-yl)-N-propyl-isophthalamic acid methyl ester (100 mg, 0.32 mmol) in methanol (10 mL). Dropwise add 1 N lithium hydroxide (0.38 mL) and stir overnight at room temperature. Add 2 N NaOH (0.1 mL) and stir for 48 h at room temperature. Acidify the mixture to about pH=6 by DOWEX® 50WX2-100 ion exchange resin and filter. Concentrate filtrate and lyophilize (1:1 acetonitrile:water) to give the title compound.

Workup

  1. filtrationfilter

Sources & evidence

ORD record
ord-b7b28d4dfa814e40a5acd32a0cd00711
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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