Hydrochloric Acid → N-acetylanthranilic acid

HRID 1729639

Reaction equation

HRID 1729639 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[C:13](OC(=O)C)(=O)C.Cl>>[C:5]([NH:6][C:7]1[C:1](=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:2]([OH:4])=[O:3])(=[O:12])[CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8359Isatoic Anhydride

Product 1

HCID 6971N-acetylanthranilic acidYield 94%

Procedure

The isatoic anhydride and acetic anhydride were combined in a three necked, round bottomed flask equipped with a mechanical stirrer, dropping funnel, thermometer, reflux condenser and drying tube. The acetic anhydride was added to the mixture through the dropping funnel over a period of 30 minutes. The reaction was heated to 90°-100° C for 1.5 hours and then cooled to room temperature. The cooled reaction mixture was poured into a kilogram of ice containing 150 ml of concentrated hydrochloric acid. The white solid which precipitated was isolated, washed with 200 ml of water and dried to give 51.5 parts (94% yield) of N-acetylanthranilic acid having m.p. 183°-185° C.

Workup

  1. customround bottomed flask equipped with a mechanical stirrer
  2. temperaturethermometer, reflux condenser
  3. customdrying tube
  4. additionThe acetic anhydride was added to the mixture through the dropping funnel over a period of 30 minutes
  5. temperatureThe reaction was heated to 90°-100° C for 1.5 hours
  6. customThe cooled reaction mixture
  7. customThe white solid which precipitated
  8. customwas isolated
  9. washwashed with 200 ml of water
  10. customdried

Sources & evidence

ORD record
ord-fdb85c3739a348a795ae772ce27ea6a3
Source dataset
uspto-grants-1976_11
Patent number
US03989698

Linked notes

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