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

HRID 234897Notes

Reaction equation

HRID 234897 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]([CH3:14])[C:11](=[O:15])[NH:10][C:9]=2[CH:16]=1)=[O:4].[H-].[Na+].[CH2:19](I)[CH3:20].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:10]1[C:9]2[CH:16]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[CH:7][C:8]=2[O:13][CH:12]([CH3:14])[C:11]1=[O:15])[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10656590methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Product 1

HCID 10562564Methyl 4-ethyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-6-carboxylateYield 80.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (2.2 g) in dimethylformamide (20 ml) were added 60% sodium hydride (in oil) (0.5 g) and ethyl iodide (1.8 g) and the mixture was stirred at room temperature for a day. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure and the resulting residue was subjected to purification by column chromatography using ethyl acetate/hexane [1:1 (v/v)] to give 4-ethyl-6-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (2.0 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was subjected to purification by column chromatography

Sources & evidence

ORD record
ord-91f57d15239046dabba8517a557f58e9
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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