Sodium Hydroxide → 5-(9-Carboxynona-6,8-dienyl)imidazo[1,5-a]pyridine

HRID 280211Notes

Reaction equation

HRID 280211 reaction equation
C([O:3][C:4]([CH:6]=[CH:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[N:20]2[CH:21]=[N:22][CH:23]=[C:19]2[CH:18]=[CH:17][CH:16]=1)=[O:5])C.[OH-].[Na+]>CO>[C:4]([CH:6]=[CH:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[N:20]2[CH:21]=[N:22][CH:23]=[C:19]2[CH:18]=[CH:17][CH:16]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 540559275-(9-Ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine

Product 1

HCID 538731915-(9-Carboxynona-6,8-dienyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6 g 5-(9-ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine in 30 ml of methanol is added 6 ml of 1N sodium hydroxide. The reaction is allowed to stir at room temperature for 3 hours. The methanol is evaporated under reduced pressure and the residue diluted with 15 ml water and the solution adjusted to pH 7 with 1N hydrochloric acid. The solution is extracted with 2×150 ml of ethyl acetate. The combined ethyl acetate extracts are dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield 5-(9-carboxynona-6,8-dienyl)imidazo[1,5-a]pyridine melting at 120°-122°.

Workup

  1. customThe methanol is evaporated under reduced pressure
  2. additionthe residue diluted with 15 ml water
  3. extractionThe solution is extracted with 2×150 ml of ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-14be7a2dc72749b693db0dc6d469291d
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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