Pyridine → Acetanthranil

HRID 1729638Notes

Reaction equation

HRID 1729638 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=O)[O:4][C:2]2=[O:3].N1C=CC=C[CH:14]=1>>[CH3:14][C:5]1[O:4][C:2](=[O:3])[C:1]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 8359Isatoic Anhydride

Product 1

HCID 68236AcetanthranilYield 86%

Conditions

Temperature
45 °C

Procedure

The isatoic anhydride and pyridine were combined in a round bottomed, 3-necked flask equipped with a mechanical stirrer, thermometer, reflux condenser, dropping funnel and drying tube. The isatoic anhydride suspension was heated to 45° C and the acetic anhydride was added over a period of 30 minutes. Carbon dioxide evolution occurred during the addition of the acetic anhydride. The reaction mixture was heated to 90° C for 1.5 hours. The evolution of carbon dioxide stopped. The reaction mixture was concentrated under reduced pressure (15 mm. of Hg). The residue was crystallized from 100 ml of cyclohexane to give 42 parts by weight (86% yield) of 2-methyl-4H-3,1-benzoxazine-4-one with m.p. 79°-81° C.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer, reflux condenser
  3. customdrying tube
  4. additionthe acetic anhydride was added over a period of 30 minutes
  5. additionCarbon dioxide evolution occurred during the addition of the acetic anhydride
  6. temperatureThe reaction mixture was heated to 90° C for 1.5 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure (15 mm. of Hg)
  8. customThe residue was crystallized from 100 ml of cyclohexane

Sources & evidence

ORD record
ord-ebbae00182354e9c9236fbf9202acfbe
Source dataset
uspto-grants-1976_11
Patent number
US03989698

Reaction notes

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