Hippuric Acid → Azlactone

HRID 264781Notes

Reaction equation

HRID 264781 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C(OC(=O)C)(=O)C>>[C:6]1([C:4]2[O:13][C:1](=[O:12])[CH2:2][N:3]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 464Hippuric AcidHCID 7918Acetic Anhydride

Product 1

HCID 65073Azlactone

Conditions

Temperature
80 °C

Procedure

657 gm (3.66 mol) of hippuric acid and 2,618 gm of acetic anhydride were charged into a 5 1 glass reaction vessel, and heated at 80° C. for 15 minutes. When the reaction liquid became transparent, the reaction vessel was placed into a water bath to lower the internal temperature to 30° C., followed by cooling to 0° C. on a dry ice-methanol bath.

Workup

  1. customWhen the reaction liquid
  2. customthe reaction vessel was placed into a water bath
  3. customto 30° C.
  4. temperatureby cooling to 0° C. on a dry ice-methanol bath

Sources & evidence

ORD record
ord-12ba796543474e9985980c22ae46cfd2
Source dataset
uspto-grants-1997_07
Patent number
US05646291

Reaction notes

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