Water → 4-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234904Notes

Reaction equation

HRID 234904 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[NH:9][C:10](=[O:13])[CH2:11][O:12][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH2:18](I)[CH3:19].O>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([N:9]1[C:8]2[CH:14]=[CH:15][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=2[O:12][CH2:11][C:10]1=[O:13])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10845978Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

Product 1

HCID 107761024-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineYield 26.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine [prepared in Preparation 4(1)] (1.0 g) in dimethylformamide (80 ml) were added 60% sodium hydride (in oil) (0.25 g) and ethyl iodide (1.0 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 recrystallized from ethyl acetate/hexane to give 4-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (0.3 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b0c323f87f274e5c912556c8f1bc1267
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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