Iodine → 5-Chloro-3,3-diMethylindoline

HRID 1189477Notes

Reaction equation

HRID 1189477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=O)[C:5]2([CH3:13])[CH3:12].[BH4-].[Na+].II.[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][C:5]2([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 127000715-chloro-3,3-dimethyl-indolin-2-one

Product 1

HCID 218361745-Chloro-3,3-diMethylindolineYield 82.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of 630 mg of 5-chloro-3,3-dimethyl-1,3-dihydro-2H-indole-2-one in 6.30 mL of tetrahydrofuran was added 609 mg of sodium borohydride, followed by stirring for 10 minutes. Then, a solution of 1.63 g of iodine in 3.78 mL of tetrahydrofuran was added dropwise thereto at −10° C. or lower under cooling in an ice-acetone bath, followed by stirring at the same temperature for 30 minutes, then warming to room temperature, and stirring overnight. After diluting with chloroform, a saturated aqueous ammonium chloride solution was added dropwise thereto. The aqueous layer was separated and then the organic layer was washed with a saturated aqueous sodium sulfite solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 480 mg of 5-chloro-3,3-dimethylindoline as a colorless oily substance.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. temperaturewarming to room temperature
  3. stirringstirring overnight
  4. customThe aqueous layer was separated
  5. washthe organic layer was washed with a saturated aqueous sodium sulfite solution
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-64ec7c7fe8ce4f4588b5598a17eb89a9
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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