Ethyl Acetate → Methyl 2,2-dimethyl-3-oxo-3,4-dihydro-2h-1,4-benzoxazine-6-carboxylate

HRID 234894

Reaction equation

HRID 234894 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].C(OCC)(=O)C.C(=O)([O-])O.[Na+].Br[C:25]([CH3:30])([CH3:29])[C:26](Br)=[O:27]>O>[CH3:29][C:25]1([CH3:30])[C:26](=[O:27])[NH:1][C:2]2[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=2[O:12]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 886852-Bromo-2-methylpropionyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 10513902Methyl 2,2-dimethyl-3-oxo-3,4-dihydro-2h-1,4-benzoxazine-6-carboxylateYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To solution of 2-amino-4-methoxycarbonylphenol [Acta Chimica Academiae Scientiarum Hungaricae, 99 (1), 49-50 (1979)] (4.78 g) in a mixed solvent of ethyl acetate (50 ml) and water (50 ml) were added sodium hydrogen carbonate (3.6 g) and 2-bromoisobutyryl bromide (6.90 g) and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in dimethylformamide (70 ml), to the solution was added potassium carbonate (4.35 g) and the mixture was stirred at room temperature for a day. The reaction solution was poured into water to give precipitates, which were taken by filtration and dried to give 2,2-dimethyl-6-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (5.4 g).

Workup

  1. customThe organic layer was separated
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in dimethylformamide (70 ml), to the solution
  4. additionwas added potassium carbonate (4.35 g)
  5. stirringthe mixture was stirred at room temperature for a day
  6. additionThe reaction solution was poured into water
  7. customto give
  8. customprecipitates
  9. filtrationwhich were taken by filtration
  10. customdried

Sources & evidence

ORD record
ord-c62b92fd63cc49bab014604fcad2e63b
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Linked notes

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