Anthranilic Acid → 2-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-one

HRID 497975Notes

Reaction equation

HRID 497975 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:11]=[C:12]1[O:16][C:14](=O)[CH2:13]1.C(OC(=O)C)(=O)C>CC(C)=O.O1CCCC1>[O:16]=[C:12]([CH3:11])[CH2:13][C:14]1[O:9][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1

Participants

6

Reactant 3

HCID 227Anthranilic AcidHCID 7918Acetic AnhydrideHCID 12661Diketene

Product 1

HCID 159380972-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-oneYield 57.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of anthranilic acid (290 g, 2.1 mol) in acetone (1000 mL), diketene (460 mL, 6.0 mol) was added dropwise at room temperature. The solution was stirred at room temperature for 16 hours, and the resulting crystals were collected by filtration, washed with acetone and diethylether, and air dried (170 g yield). The crude crystals were suspended in a mixture of acetic anhydride (320 mL, 3.4 mol) and tetrahydrofuran (1000 mL), and the suspension was heated and stirred at 80° C. for 12 hours. The suspension was cooled to room temperature, and concentrated under reduced pressure, and the resulting crude crystals were collected by filtration. The crystals were washed with acetonitrile and air dried to give the title compound (244 g, 57% yield).

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed with acetone and diethylether, and air
  3. customdried
  4. custom(170 g yield)
  5. temperaturethe suspension was heated
  6. stirringstirred at 80° C. for 12 hours
  7. temperatureThe suspension was cooled to room temperature
  8. concentrationconcentrated under reduced pressure
  9. filtrationthe resulting crude crystals were collected by filtration
  10. washThe crystals were washed with acetonitrile and air
  11. customdried

Sources & evidence

ORD record
ord-c04153c765484fc49472639563da51f8
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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