Hydrochloric Acid → 2-(Propan-2-yl)imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 1468261Notes

Reaction equation

HRID 1468261 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]2[CH:11]=C(C#N)[CH:9]=[CH:8][N:7]2[CH:14]=1)([CH3:3])[CH3:2].[OH-:15].[Li+].Cl.[CH2:18]([OH:20])[CH3:19]>>[CH:1]([C:4]1[N:5]=[C:6]2[CH:11]=[C:19]([C:18]([OH:15])=[O:20])[CH:9]=[CH:8][N:7]2[CH:14]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 680113302-Isopropylimidazo[1,2-a]pyridine-7-carbonitrile

Product 1

HCID 643960682-(Propan-2-yl)imidazo[1,2-a]pyridine-7-carboxylic acidYield 83%

Procedure

2-Isopropylimidazo[1,2-a]pyridine-7-carbonitrile (15.9 g, 85.8 mmol) obtained in step 1 was dissolved in a 50% ethanol aqueous solution (80 mL). Under water-cooled condition, lithium hydroxide.1 hydrate (7.20 g, 172 mmol) was added, and the mixture was stirred under heat and reflux for 3 hours. Under ice-cooled condition, 3 mol/L hydrochloric acid (62 mL) was added to the reaction mixture. The precipitated crystals were collected by filteration, washed with water, and dried to give 2 isopropylimidazo[1,2-a]pyridine-7-carboxylic acid (14.6 g, yield 83%).

Workup

  1. temperatureunder heat
  2. temperaturereflux for 3 hours
  3. additionwas added to the reaction mixture
  4. customThe precipitated crystals were collected by filteration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7a5f59fd57ab430eb1b5fe189db28a2b
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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