Hydrochloric Acid → 6-Bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylic acid

HRID 908220Notes

Reaction equation

HRID 908220 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:12]([Br:13])=[CH:11][N:10]2[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=[C:9]2[CH:8]=1)=[O:6].Cl>O.C(O)C>[Br:13][C:12]1[C:7]([C:5]([OH:6])=[O:4])=[CH:8][C:9]2[N:10]([CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67041599Methyl 6-bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylate

Product 1

HCID 670418506-Bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

NaOH (1N, 61 ml) was added to a suspension of 6-bromo-2-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (10.11 g, 31 mmol) in a mixture of water (30 ml) and ethanol (60 ml), and the mixture was heated to reflux (2 h). The mixture was cooled (0° C.) and HCl (conc., ˜10 ml) was slowly added. The dark brown suspension was filtered, washed with a small amount of ethanol, and dried under vacuum. The obtained title compound (9.47 g, 98%) was used in the next step without further purification. MS (m/e)=318.9 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux (2 h)
  3. additionwas slowly added
  4. filtrationThe dark brown suspension was filtered
  5. washwashed with a small amount of ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0e5ef9135e194e00b387ff9a5d7509ef
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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