Hydrochloric Acid → 2-Phenylimidazo[1,2-a]pyridine-7-carboxylic acid

HRID 908204Notes

Reaction equation

HRID 908204 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=[C:9]2[CH:8]=1)=[O:6].Cl>C(O)C.O>[C:16]1([C:14]2[N:15]=[C:9]3[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:12]=[CH:11][N:10]3[CH:13]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 352572Methyl 2-phenylimidazo[1,2-a]pyridine-7-carboxylate

Product 1

HCID 3525732-Phenylimidazo[1,2-a]pyridine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of NaOH in water (1N, 54 ml, 54 mmol) was added to a suspension of 2-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (6.8 g, 27 mmol) in a mixture of ethanol (50 ml) and water (25 ml). The mixture was heated to reflux (2 h). The obtained clear solution was cooled, poured onto crushed ice (50 g); HCl (25%, 10 ml) was added. The mixture was then filtered, and the precipitate was washed (ethanol) and dried under vacuum. The obtained solid (6.36 g, 99%) was used in the next step without further purification. MS (m/e)=239.1 [M+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux (2 h)
  3. temperatureThe obtained clear solution was cooled
  4. additionpoured
  5. filtrationThe mixture was then filtered
  6. washthe precipitate was washed (ethanol)
  7. customdried under vacuum
  8. customThe obtained solid (6.36 g, 99%) was used in the next step without further purification

Sources & evidence

ORD record
ord-a2eefe1f9d544b459e2a1fe797a1555b
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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