Diethyl Ether → 4,7-dichloro-1-pentyl-1H-indole-2,3-dione

HRID 425522Notes

Reaction equation

HRID 425522 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[NH:8]2.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(OCC)C>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[N:8]2[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 27347934,7-Dichloroisatin

Product 1

HCID 666426684,7-dichloro-1-pentyl-1H-indole-2,3-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (5.00 mL) was added a solution of 4,7-dichloro-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in N,N-dimethylformamide (5.00 mL) at 0° C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N,N-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2×20.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, 98%): MS (ES+) m/z 286.2 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  2. customAfter the organic layer was separated
  3. washit was washed with water (2×20.0 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe gummy residue was dried under vacuum
  8. customthe solid was triturated with ether

Sources & evidence

ORD record
ord-881d6e49989d46a9afb622e78d1f0458
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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