Water → 8-Bromo-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 598065Notes

Reaction equation

HRID 598065 reaction equation
Br[CH:2]([CH3:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[C:7]=1[OH:13])=[O:4].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:12][C:8]1[C:7]2[O:13][CH:2]([CH3:14])[C:3](=[O:4])[NH:5][C:6]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 672670902-Bromo-N-(3-bromo-2-hydroxyphenyl)propionamide

Product 1

HCID 672673248-Bromo-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-N-(3-bromo-2-hydroxyphenyl)propionamide (4.70 g, 14.6 mmol) and potassium carbonate (2.01 g, 14.6 mmol) in N,N-dimethylformamide (100 ml) was stirred at room temperature for 15 h. The mixture was poured into water and extracted with ether. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 20% ethyl acetate/n-hexane to afford 2.12 g (60%) of the title compound.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography
  6. washeluting with 20% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-c2bdb171b3ff42af8683aa03ba3fbb2e
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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