Acetonitrile → 2,3-dihydro-1H-indol-1-amine

HRID 1742043Notes

Reaction equation

HRID 1742043 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(#[N:9])C.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1.NOS(O)(=O)=O>O>[NH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10328IndolineHCID 11430Potassium CarbonateHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 27609322,3-dihydro-1H-indol-1-amineYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 40 ml of water was dissolved 2.76 g(20 mmol) of potassium carbonate thoroughly, and 10 ml of acetonitrile and 2.24 ml(20 mmol) of indoline were added thereto in this order. After stirring the reaction mixture for 10 min, 2.26 g(20 mmol) of hydroxylamine-O-sulfonic acid was added thereto. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated under the reduced pressure. The concentrate was extracted with dichloromethane and treated with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under the reduced pressure, and the resulting concentrate was subjected to chromatography over silica gel using dichloromethane as an eluent. The fractions were concentrated to give 0.99 g of the desired compound(37%).

Workup

  1. stirringAfter stirring at room temperature for 1.5 hours
  2. concentrationthe reaction mixture was concentrated under the reduced pressure
  3. extractionThe concentrate was extracted with dichloromethane
  4. additiontreated with anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under the reduced pressure
  7. concentrationthe resulting concentrate
  8. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-5d6014d5155741928116afe5c45124ac
Source dataset
uspto-grants-1994_08
Patent number
US05336673

Reaction notes

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