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Hydrochloric Acid → 2-Bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acid

HRID 60124
Notes
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Reaction equation

HRID 60124 reaction equation
[OH-].[Na+].[Br:3][C:4]1[N:5]=[C:6]2[CH2:11][CH:10]([C:12]([O:14]C)=[O:13])[CH2:9][CH2:8][N:7]2[CH:16]=1.Cl>CO>[Br:3][C:4]1[N:5]=[C:6]2[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9][CH2:8][N:7]2[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90383213Methyl 2-bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylate

Product 1

HCID 903832892-Bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acidYield 58.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A 1 N sodium hydroxide aqueous solution (23 ml) was added to a methanol (23 ml) solution of the methyl 2-bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylate (6.3 g) obtained in (Example 2.7) <Step 2>, and the obtained mixture was then stirred at 40° C. for 1 hour. Thereafter, 1 N hydrochloric acid (23 ml) was added to the reaction solution, and the generated solid was then collected by filtration, followed by washing with water (20 ml). The obtained solid was subjected to azeotropy with toluene, and was then dried under reduced pressure, so as to obtain the title compound (3.5 g) in the form of a beige solid.

Workup

  1. customobtained in (Example 2.7) <Step 2>
  2. filtrationthe generated solid was then collected by filtration
  3. washby washing with water (20 ml)
  4. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-3b9c5aa635e14f55b2417667bc413cb8
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440970B2

Reaction notes

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