Water → 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylic acid

HRID 406323Notes

Reaction equation

HRID 406323 reaction equation
[OH-:1].[Li+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11]#N)[CH:8]=[CH:7][C:6]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1.[OH2:19]>>[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11]([OH:19])=[O:1])[CH:8]=[CH:7][C:6]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1

Participants

4

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 666080866-Methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinonitrile

Product 1

HCID 666084476-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylic acid

Procedure

Lithium hydroxide powder (13 g) was added to a suspension of 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbonitrile (52.4 g) in water (464 mL), and the mixture was heated under reflux for three hours. The reaction solution was left to cool to room temperature. The reaction solution was filtered through celite, and the celite was washed with water (100 mL×4). Concentrated hydrochloric acid was added to the filtrate under ice-cooling to adjust the pH to 4 to 5. The precipitated powder was collected by filtration. The resulting powder was washed with water and then air-dried for three days to obtain 51.9 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for three hours
  3. waitThe reaction solution was left
  4. filtrationThe reaction solution was filtered through celite
  5. washthe celite was washed with water (100 mL×4)
  6. additionConcentrated hydrochloric acid was added to the filtrate under ice-
  7. temperaturecooling
  8. filtrationThe precipitated powder was collected by filtration
  9. washThe resulting powder was washed with water
  10. customair-dried for three days

Sources & evidence

ORD record
ord-9560d81b854d43eebbe050200427261e
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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