Hydrochloric Acid → 5-Bromo-7-nitroindoline

HRID 1173101

Reaction equation

HRID 1173101 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

5.05 g (17.7 mmol) of 1-acetyl-5-bromo-7-nitroindoline was dissolved into a mixed solution of 6 ml of ethanol and 40 ml of 6 N hydrochloric acid, followed by heating under reflux for 3 hours. After neutralizing by adding sodium carbonate thereto, the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 4.13 g of 5-bromo-7-nitroindoline. 301 mg (1.24 mmol) of this compound was added to 10 ml of toluene, and then 580 mg (2.55 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added thereto. After heating under reflux for 3.5 hours while stirring, the insoluble matters were filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 252 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fead91756ba84e9b8e4ae62d4d3fbe5d
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Linked notes

Loading…