Hippuric Acid → HCID 301280, compound

HRID 1065543Notes

Reaction equation

HRID 1065543 reaction equation
[C:1]([NH:9][CH2:10][C:11](O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](=[O:17])(O)[O-:15].[K+].C(O[C:23](=O)[CH3:24])(=O)C>O>[C:2]1([C:1]2[O:15][C:14](=[O:17])[C:10](=[CH:11][C:2]3[CH:1]=[N:9][CH:10]=[CH:23][CH:24]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 464Hippuric AcidHCID 7918Acetic AnhydrideHCID 516893Potassium Bicarbonate

Product 1

HCID 301280HCID 301280, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Phenyl-4-(3-pyridylmethyl)oxazolone. A mixture of 180 g of N-benzoyl glycine, 40 g of potassium bicarbonate and 400 ml of acetic anhydride was stirred until solution occurred. 3-Pyridylaldehyde (100 ml) was then added and the mixture stirred for 1 hr with maintenance of the temperature at 20°-25° C. by means of a cold water bath. The mixture was poured into 2 liters of hot water and the precipitate collected by filtration and dried to afford 2-phenyl-4-(3-pyridylmethylene)-2-oxazolin-5-one, mp 164.5° C. The material was hydrogenated in tetrahydrofuran solution over 20% palladium-on-carbon. The catalyst was removed by filtration and the solvent evaporated in vacuo to give the azlactone as a tan foam.

Workup

  1. stirringthe mixture stirred for 1 hr with maintenance of the temperature at 20°-25° C. by means of a cold water bath
  2. filtrationthe precipitate collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-1d156dd8b08c4609a47bf4890166652c
Source dataset
uspto-grants-1982_05
Patent number
US04329473

Reaction notes

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