Hydrochloric Acid → 6-Bromo-7-methyl-1H-indole-2,3-dione

HRID 2105111Notes

Reaction equation

HRID 2105111 reaction equation
CCO[CH:4]([OH:9])[C:5](Cl)(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+].[Br:17][C:18]1[C:19]([CH3:25])=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].Cl.N[OH:28].Cl>O>[Br:17][C:18]1[C:19]([CH3:25])=[C:20]2[C:22]([C:4](=[O:9])[C:5](=[O:28])[NH:21]2)=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10587Chloral alcoholateHCID 24436Sodium SulfateHCID 1235383-Bromo-o-toluidineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 112301886-Bromo-7-methyl-1H-indole-2,3-dioneYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Chloral alcoholate (0.43 g, 1.05 eq) and Na2SO4 (2.84 g, 20 mmol) were dissolved in 10 mL water. 3-Bromo-2-methylaniline (0.33 g, 1.77 mmol) was added to the solution followed by 0.16 mL conc. HCl aqueous solution and NH2OH.HCl (0.38 g, 3.0 eq). The mixture was refluxed for 15 min and stirring was continued for additional 1 hr at RT. The precipitate was collected by filtration, washed with water and dried under vacuum. This precipitate was dissolved in 1 mL H2SO4 and the solution was heated (80° C.) for 15 min. After cooling down to RT, the mixture was poured into ice-water mixture and the precipitate was collected, washed with water and dried under vacuum to give the title compound (0.26 g, 61%).

Workup

  1. temperatureThe mixture was refluxed for 15 min
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. dissolutionThis precipitate was dissolved in 1 mL H2SO4
  6. temperatureAfter cooling down to RT
  7. additionthe mixture was poured into ice-water mixture
  8. customthe precipitate was collected
  9. washwashed with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-a1546dec27d54d6eb55f790aea55d5fd
Source dataset
uspto-grants-2009_08
Patent number
US07579313B2

Reaction notes

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