Water → 7-methoxycarbonyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234892Notes

Reaction equation

HRID 234892 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+].I[CH:19]([CH3:21])[CH3:20].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[N:9]([CH:19]([CH3:21])[CH3:20])[C:10](=[O:13])[CH2:11][O:12][C:7]=2[CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 10845978Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

Product 1

HCID 107292827-methoxycarbonyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazineYield 24.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (1.00 g) in dimethylformamide (10 ml) were added 60% sodium hydride (in oil) (0.25 g) and 2-iodopropane (1.00 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 [1:4 (v/v)] to give 7-methoxycarbonyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (0.30 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-4f34d54e5da045adb985518976f9e1a0
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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