2-Bromo-5-methoxybenzoic acid → 6-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 557131Notes

Reaction equation

HRID 557131 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O-:13][C:14]#[N:15].[K+]>N1C=CC=CC=1.[Cu]Br>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:15][C:14](=[O:13])[O:6][C:4](=[O:5])[C:3]=2[CH:7]=1

Participants

5

Reactant 2

HCID 899062-Bromo-5-methoxybenzoic acidHCID 11378442Potassium cyanate

Product 1

HCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 1049PyridineSolvent

Procedure

5.00 g (21.6 mmol) 2-Bromo-5-methoxy-benzoic acid, 620 mg (4.32 mmol) copper (I) bromide and 2.63 g (32.4 mmol) potassium cyanate were dissolved in pyridine and boiled for 30 min. The solvent was removed and the residue was dissolved in 150 ml 2N hydrogen chloride acid and 150 ml ethyl acetate. The organic solvent was treated with water and brine, dried over magnesium sulfate and removed. The residue was digested with methanol.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in 150 ml 2N hydrogen chloride acid
  3. additionThe organic solvent was treated with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customremoved

Sources & evidence

ORD record
ord-750182114b4e45759498917073504d29
Source dataset
uspto-grants-2011_11
Patent number
US08058431B2

Reaction notes

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