Water → methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 234896Notes

Reaction equation

HRID 234896 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(=O)([O-])[O-].[K+].[K+].Cl[CH:20]([CH3:24])[C:21](Cl)=[O:22].O>CN(C)C=O.C(OCC)(=O)C>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:12][CH:20]([CH3:24])[C:21](=[O:22])[NH:1][C:2]=2[CH:7]=1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 11430Potassium CarbonateHCID 1110192-Chloropropionyl chloride

Product 1

HCID 10656590methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylateYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-amino-4-methoxycarbonylphenol [Acta Chimica Academiae Scientiarum Hungaricae, 99(1), 49-50 (1979)] (5.0 g) in dimethylformamide (30 ml) were added potassium carbonate (8.3 g) and 2-chloropropionyl chloride (4.0 g) and the mixture was stirred at 50° C. for 2 hours. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The extraction was concentrated and hexane was added thereto to give precipitates, which were taken by filtration and dried to give 6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (4.7 g).

Workup

  1. extractionThe extraction
  2. concentrationwas concentrated
  3. additionhexane was added
  4. customto give
  5. customprecipitates
  6. filtrationwhich were taken by filtration
  7. customdried

Sources & evidence

ORD record
ord-834a2a3c29424ed6bb03e48c07199506
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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