Dimethylformamide → 3,4-Dihydro-7-hydroxy-4-[2-(3,4-dimethoxyphenyl)ethyl]-1,4-benzoxazine-3-one

HRID 893025Notes

Reaction equation

HRID 893025 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.[C:16]([O:19][CH2:20][CH3:21])(=O)C.[CH3:22][N:23](C)[CH:24]=[O:25]>>[OH:12][C:9]1[CH:8]=[CH:7][C:22]2[N:23]([CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=3)[C:24](=[O:25])[CH2:16][O:19][C:20]=2[CH:21]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 114706023,4-Dimethoxyphenethyl bromide

Product 1

HCID 539344153,4-Dihydro-7-hydroxy-4-[2-(3,4-dimethoxyphenyl)ethyl]-1,4-benzoxazine-3-one

Procedure

A solution of the amide (0.50 mmol) was added to a mixture of sodium hydride (2.3 mmol) and dimethyl formamide (2.0 ml). After stirring for 30 min a solution of 1-bromo-2-(3,4-dimethoxyphenyl)ethane (0.50 mmol) in dimethyl formamide (1.0 ml) was added at 0° C. After 2 h an aqueous workup with ethyl acetate was performed. The organic layers were dried with magnesium sulfate and concentrated. Purification by flash chromatography provided the title compound.

Workup

  1. additionwas added at 0° C
  2. dry with materialThe organic layers were dried with magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-eb8af7120b0a4fb68308e39c933e5e17
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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