Hydrochloric Acid → 5-Bromo-3-(tert-butylamino)quinoxaline-2-carboxylic acid

HRID 1056250Notes

Reaction equation

HRID 1056250 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]([CH:12]=[O:13])=[N:7]2.[OH-:19].[Na+].OO.Cl>CO.OO.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]([C:12]([OH:19])=[O:13])=[N:7]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 897823205-Bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde

Product 1

HCID 897819945-Bromo-3-(tert-butylamino)quinoxaline-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a slurry of 5-bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde (306a) (250 mg, 0.81 mmol) in MeOH (0.4 mL) and NaOH 1.0 N (1.62 mL, 1.62 mmol) was added two drops H2O2 30% in water (0.10 mL, 1.01 mmol) from a pasteur pipette. The reaction was stirred rapidly at RT and became a yellow/orange solution. Additional 0.05 mL 30% aq H2O2 was added. After 30 min, additional 0.05 mL 30% aq H2O2 was added. After 30 min, the reaction mixture was treated with ice, acidified to pH <2 with 1.0 N HCl, and diluted with 10 mL water. The orange suspension was filtered, rinsing with 10 mL of water to give 5-bromo-3-(tert-butylamino)quinoxaline-2-carboxylic acid (0.26 g, 0.80 mmol, 99% yield) as an orange solid. m/z (ESI, +ve ion) 324.0/326.0 (M+H)+.

Workup

  1. waitAfter 30 min
  2. additionthe reaction mixture was treated with ice
  3. filtrationThe orange suspension was filtered
  4. washrinsing with 10 mL of water

Sources & evidence

ORD record
ord-830c6c6fa6d2489197655f069ada12af
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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