Water → HCID 22247294, compound

HRID 1107980Notes

Reaction equation

HRID 1107980 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14](Br)=[C:15]([CH3:21])[C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cu](C#N)[C:24]#[N:25].C(OCC)(=O)C.O>CN1CCCC1=O>[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:24]#[N:25])=[C:15]([CH3:21])[C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 22247351HCID 22247351, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 22247294HCID 22247294, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

1-Octyl-5-bromo-6-methyl-7-nitroindoline (4.0 g) was dissolved in N-methylpyrrolidone (40 ml), and copper cyanide (1.9 g) was added, which was followed by stirring at 190° C. for 1 hr. Ethyl acetate (100 ml) and water (100 ml) were added to the reaction mixture. The insoluble matter was filtered off. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5-1/3) to give 2.4 g of oily 1-octyl-5-cyano-6-methyl-7-nitroindoline.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. washThe ethyl acetate layer 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 silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5-1/3)

Sources & evidence

ORD record
ord-9d6690f40951450eb906e4bc409cfbc4
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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