Ethyl Acetate → HCID 22247351, compound

HRID 1531992Notes

Reaction equation

HRID 1531992 reaction equation
[Br:1][C:2]1[CH2:10][C:9](C)([N+:11]([O-:13])=[O:12])[C:8]2[NH:7][CH2:6][CH2:5][C:4]=2[CH:3]=1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[C:26](OCC)(=O)C>CN(C)C=O>[CH2:18]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[C:10]([CH3:26])[C:9]=2[N+:11]([O-:13])=[O:12])[CH2:5][CH2:6]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 69628847HCID 69628847, compound

Product 1

HCID 22247351HCID 22247351, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-7-methyl-7-nitroindoline (3.6 g) was dissolved in N,N-dimethylformamide (36 ml), and sodium hydride (677 mg) was added, which was followed by stirring at room temperature for 0.5 hr. 1-Iodooctane (3.4 g) was added to the reaction mixture and the mixture was stirred at the same temperature for 24 hr. Ethyl acetate (200 ml) was added to the reaction mixture, and the mixture was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated under reduced pressure. The residue was purified by gel column chromatography (eluent: ethyl acetate/n-hexane=1/100−1/50) to give 4.0 g of oily 1 -octyl-5-bromo-6-methyl-7-nitroindoline.

Workup

  1. stirringthe mixture was stirred at the same temperature for 24 hr
  2. washthe mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEthyl acetate was evaporated under reduced pressure
  5. customThe residue was purified by gel column chromatography (eluent: ethyl acetate/n-hexane=1/100−1/50)

Sources & evidence

ORD record
ord-360539f620a94ea08b57346e5faa13e2
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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