Hydrochloric Acid → 5-Bromo-7-nitroindoline

HRID 863437

Reaction equation

HRID 863437 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:16])=[CH:10][C:11]=2[N+:13]([O-:15])=[O:14])[CH2:6][CH2:5]1)(=O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:16][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)[NH:4][CH2:5][CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27292431-Acetyl-5-bromo-7-nitroindoline

Product 1

HCID 30189115-Bromo-7-nitroindolineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Acetyl-5-bromo-7-nitroindoline (5.05 g, 17.7 mmol) was added to a mixture comprising 6 ml of ethanol and 40 ml of 6N hydrochloric acid. The obtained mixture was heated under reflux for 3 hours, neutralized with sodium carbonate and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 4.13 g of 5-bromo-7-nitroindoline. This compound (301 mg, 1.24 mmol) was added to 10 ml of toluene, followed by the addition of 580 mg (2.55 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The obtained mixture was refluxed by heating under stirring for 3.5 hours and filtered to remove insolubles. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography to give 252 mg of the title compound.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a5cea643742e48a282769fa1d2297dfd
Source dataset
uspto-grants-1998_02
Patent number
US05721246

Linked notes

Loading…