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

HRID 234890Notes

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+].I[CH:20]([CH3:22])[CH3:21].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH:20]([CH3:22])[CH3:21])[C:10](=[O:14])[CH:11]([CH3:13])[O:12][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (prepared in Preparation 1) (6.1 g) in dimethylformamide (120 ml) were added 60% sodium hydride (in oil) (1.1 g) and 2-iodopropane (4.3 g) and the mixture was stirred at 60° C. for 5 hours. 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-2-methyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (3.1 g).

Workup

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

Sources & evidence

ORD record: ord-15df023a0fda4d77a2e442bf1a3bed12
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05597820

Reaction notes

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