Sodium Hydroxide → 5-(4-Carboxybuta-1,3-dienyl)-imidazo[1,5-a]pyridine

HRID 280203Notes

Reaction equation

HRID 280203 reaction equation
C([O:3][C:4]([CH:6]=[CH:7][CH:8]=[CH:9][C:10]1[N:15]2[CH:16]=[N:17][CH:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1)=[O:5])C.[OH-].[Na+]>CO>[C:4]([CH:6]=[CH:7][CH:8]=[CH:9][C:10]1[N:15]2[CH:16]=[N:17][CH:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 539135015-(4-Ethoxycarbonylbuta-1,3-dienyl)imidazo[1,5-a]pyridine

Product 1

HCID 538381615-(4-Carboxybuta-1,3-dienyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 200 mg of 5-(4-ethoxycarbonylbuta-1,3-dienyl)imidazo[1,5-a]pyridine in 20 ml of methanol is added 4 ml of 1N sodium hydroxide. The reaction mixture is stirred at room temperature for 18 hours. The methanol is evaporated under reduced pressure and the residue diluted with 20 ml of water and the solution is adjusted to pH 5 with hydrochloric acid. The precipitate is collected to give 5-(4-carboxybuta-1,3-dienyl)-imidazo[1,5-a]pyridine, melting at 243°-245°.

Workup

  1. customThe methanol is evaporated under reduced pressure
  2. additionthe residue diluted with 20 ml of water
  3. customThe precipitate is collected

Sources & evidence

ORD record
ord-7e00622a39854c5db365d0fb36351fff
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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