1-Bromopropane → 5-Nitro-1-propylindoline

HRID 352335

Reaction equation

HRID 352335 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2)([O-:5])=[O:4].Br[CH2:16][CH2:17][CH3:18]>CN(C=O)C.O.CCOC(C)=O>[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)([O-:5])=[O:4]

Participants

7

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 362195-Nitroindoline

Product 1

HCID 98342765-Nitro-1-propylindoline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.51 g (12.79 mmoles) of 60% NaH is added, at 20° C., by portions, to a solution of 2 g (12.18 mmoles) of 5-nitroindoline in 16 ml of anhydrous DMF. After stirring for a further 30 minutes, 2.32 ml (25.58 mmoles) of 1-bromopropane is added dropwise. Stirring is maintained overnight and the reaction mixture is finally diluted with 50 ml of water and 50 ml of AcOEt. After stirring and decanting, the organic phase is successively washed with 25 ml of water and 25 ml of salt water, dried over Na2SO4, filtered and concentrated to dryness under vacuum. The evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 9/1). Orange oil.

Workup

  1. stirringStirring
  2. temperatureis maintained overnight
  3. stirringAfter stirring
  4. customdecanting
  5. washthe organic phase is successively washed with 25 ml of water and 25 ml of salt water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under vacuum
  9. customThe evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 9/1)

Sources & evidence

ORD record
ord-796e6a3fb63845a989e31572ba112b64
Source dataset
uspto-grants-2004_06
Patent number
US06747024B1

Linked notes

Loading…