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

HRID 234891Notes

Reaction equation

HRID 234891 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[CH2:20][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])[CH2:20][O:12][C:3]=2[CH:4]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 10845978Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylateYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 -amino-5 -methoxycarbonylphenol [Tetrahedron, 46(15), 5177-5186 (1990)] (2.20 g) in dimethylformamide (30 ml) were added potassium carbonate (4.00 g) and 2-chloroacetyl chloride (1.50 g) and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into water to give precipitates, which were taken by filtration and dried to give 7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (2.00 g).

Workup

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

Sources & evidence

ORD record
ord-3758bf8c21ed4d23b8bb6d4868a63226
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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