Water → HCID 21966469, compound

HRID 1790200Notes

Reaction equation

HRID 1790200 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]1=[O:15].[Br:16]Br.O.[OH-].[Na+]>C(O)(=O)C>[Br:16][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[CH3:12])[N:5]([CH3:13])[C:4](=[O:14])[C:3](=[O:15])[N:2]2[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 21966479HCID 21966479, compound

Product 1

HCID 21966469HCID 21966469, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1,4,6-trimethyl-1,4-dihydro-quinoxaline-2,3-dione (0.66 g, 3.2 mmol) in acetic acid (40 mL) was added bromine (0.52 g, 3.2 mmol) and the solution stirred at 50° C. overnight. The reaction mixture was cooled to room temperature and poured into water. The solution was neutralized with aqueous NaOH to Ph=7, extracted with dichloromethane and washed with brine, dried (Mg2SO4), filtered and evaporated to give 0.9 g of 6-bromo-1,4,7-trimethyl-1,4-dihydro-quinoxaline-2,3-dione used without further purification in the Suzuki coupling (step a). 1H NMR (300 MHz; CDCl3): 2.47 (s, 3 H), 3.64 (s, 6 H), 7.09 (s, 1 H), 7.40 (s, 1 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-976c401de5844f6db056c8abc7fdf8dc
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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