Isatoic Anhydride → 2-(4-Nitrophenyl)-4H-3,1-benzoxazin-4-one

HRID 543522Notes

Reaction equation

HRID 543522 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].[N+:13]([C:16]1[CH:24]=[CH:23][C:19](C(Cl)=O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>N1C=CC=CC=1>[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:5]2[O:4][C:2](=[O:3])[C:1]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 8359Isatoic Anhydride2×HCID 85024-Nitrobenzoyl chloride

Product 1

HCID 5427842-(4-Nitrophenyl)-4H-3,1-benzoxazin-4-oneYield 78.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
50 °C

Procedure

A 300 ml. flask equipped with a reflux condenser and a stirrer was charged with 16.3 g of isatoic anhydride and 150 ml of pyridine. They were stirred at about 50° C. to dissolve isatoic anhydride in pyridine. Then, 18.6 g of p-nitrobenzoylchloride was added in several portions over the course of about 10 minutes, and after the addition, the mixture was heated under reflux for 3 hours. The reaction mixture was cooled to 0° C. The precipitated crystals were separated by filtration, washed well with water, and dried at 120° C. for 4 hours by a hot air dryer. The resulting crystals were recrystallized from toluene to give 21 g of 2-p-nitrophenyl-3,1-benzoxazin-4-one.

Workup

  1. customflask equipped with a reflux condenser and a stirrer
  2. additionafter the addition
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hours
  5. temperatureThe reaction mixture was cooled to 0° C
  6. customThe precipitated crystals were separated by filtration
  7. washwashed well with water
  8. customdried at 120° C. for 4 hours by a hot air dryer
  9. customThe resulting crystals were recrystallized from toluene

Sources & evidence

ORD record
ord-49974aacd3594abf82edf0e9c493b129
Source dataset
uspto-grants-1984_05
Patent number
US04446262

Reaction notes

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