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

HRID 234893Notes

Reaction equation

HRID 234893 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[NH:9][C:10](=[O:14])[CH:11]([CH3:13])[O:12][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH2:19](I)[CH3:20].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:9]1[C:8]2[CH:15]=[CH:16][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=2[O:12][CH:11]([CH3:13])[C:10]1=[O:14])[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10798997methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

Product 1

HCID 233531704-ethyl-7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (prepared in Preparation 1) (1.00 g) in dimethylformamide (5 ml) were added 60% sodium hydride (in oil) (0.22 g) and ethyl iodide (0.78 g) and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure to give 4-ethyl-7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (0.89 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2c963547545c4c24b726925dbd23217f
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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