TCMDC_ArylPyrrole

 

Undesired products formed.

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Hydrolysis of PMY 27-1 in aqueous conditions to give the antipyrine glycanamide for coupling to pyrrole acid core. According to literature reference selective hydrolysis with catalytic base is successful, but not yield given.



Reaction Start Time: 15.00 03/01/12
PMY 27-1 and recovered SM PMY 28-1-solid (114 mg, 0.38 mmol, 1 equiv.) was stirred in water (20 mL) and sodium hydroxide (2.2 g, 55 mmol, 175 equiv.) was added and the mixture heated to reflux. After 90 minutes, TLC shows reaction complete. Mixture is now a clear, slighly pink, solution. Allowed to cool. 1H NMR not consistent with product. Shows 4-aminoantipyrine. Hydrolysis of the wrong/both amide/s.

TLC (10% MeOH/DCM) visualised with UV and vanillin:


NMR:


Reference:
J. Chem. Pharm. Res., 2010, 2(4):410-41

See also:
Hydrolysis of benzoyl protected glycinamide PMY 27-1 (PMY 28-1)
Coupling of hippuric acid and 4-aminoantipyrine using T3P (PMY 27-1)
Synthesis of hippuric acid (PMY 26-1)

Risk and Hazard Assessment:
See: Hydrolysis of benzoyl protected glycinamide PMY 27-1 (PMY 28-1)