Hydrochloric Acid → 8-Bromo-6-methyl-2-(methylthio)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 500996Notes

Reaction equation

HRID 500996 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[C:14]([Br:15])[C:9]2=[N:8][C:7]=1[S:17][CH3:18])=[O:5])C.[OH-].[Na+].Cl>C(O)C>[Br:15][C:14]1[C:9]2[N:10]([C:6]([C:4]([OH:5])=[O:3])=[C:7]([S:17][CH3:18])[N:8]=2)[CH:11]=[C:12]([CH3:16])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 684217148-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester

Product 1

HCID 220243538-Bromo-6-methyl-2-(methylthio)imidazo[1,2-a]pyridine-3-carboxylic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester (1.33 g) was dissolved in ethanol (50 mL), then a 5N aqueous sodium hydroxide solution (3 mL) was added thereto, and the mixture was stirred under reflux for 1 hour. Ice was added to the reaction mixture, then 2N hydrochloric acid (8 mL) was further added thereto, and as a result, the precipitates were obtained. The resulting precipitates were collected by filtration, washed with water, and dried under reduced pressure to give 8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridine-3-carboxylic acid (1.1 g) as a white powder.

Workup

  1. temperatureunder reflux for 1 hour
  2. additionIce was added to the reaction mixture
  3. customas a result, the precipitates were obtained
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c43db6118aa9433baf9194df8f2a9d0f
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

Loading…