Water → methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

HRID 234887Notes

Reaction equation

HRID 234887 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[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>[CH3:11][O:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:21](=[O:22])[CH:20]([CH3:24])[O:12][C:3]=2[CH:4]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1110192-Chloropropionyl chlorideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 10798997methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylateYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-methoxycarbonylphenol [Tetrahedron, 46(15), 5177-5186 (1990)] (8.3 g) in dimethylformamide (65 ml) were added potassium carbonate (20.5 g) and 2-chloropropionyl chloride (6.9 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 7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (7.78 g).

Workup

  1. customto give
  2. customprecipitates
  3. filtrationwhich were taken by filtration
  4. customdried

Sources & evidence

ORD record
ord-68d0c4cad0734286911db16b91363e0c
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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