Sodium Hydroxide → 5-(5-Carboxypent-4-enyl)-imidazo[1,5-a]pyridine

HRID 326126

Reaction equation

HRID 326126 reaction equation
C([O:3][C:4]([CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Na+]>CO>[C:4]([CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 544704715-(5-Ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine

Product 1

HCID 538080535-(5-Carboxypent-4-enyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 300 mg of 5-(5-ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine in 20 ml methanol is added 5 ml of 1 N sodium hydroxide. The reaction mixture is stirred at room temperature for 18 hours. The methanol is evaporated under reduced pressure and an additional 5 ml of water is added to the aqueous residue, which is then extracted with 3×5 ml aliquots of ethyl acetate. The basic aqueous layer is then adjusted to pH 5 and extracted with 3×5 ml portions of ethyl acetate. These extracts are dried over anhydrous magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield 5-(5-carboxypent-4-enyl)-imidazo[1,5-a]pyridine melting at 142°-144°.

Workup

  1. customThe methanol is evaporated under reduced pressure
  2. additionan additional 5 ml of water is added to the aqueous residue, which
  3. extractionis then extracted with 3×5 ml aliquots of ethyl acetate
  4. extractionextracted with 3×5 ml portions of ethyl acetate
  5. dry with materialThese extracts are dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-444033126bf243218c0e4a70064e3612
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Linked notes

Loading…