Sodium Cyanide → 1-Acetyl-3-(2-cyanoethyl)-4,6-dimethylindoline

HRID 1107957Notes

Reaction equation

HRID 1107957 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16]Br)[CH2:5]1)(=[O:3])[CH3:2].[C-:18]#[N:19].[Na+]>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][C:18]#[N:19])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 22247313HCID 22247313, compound

Product 1

HCID 222473041-Acetyl-3-(2-cyanoethyl)-4,6-dimethylindolineYield 101.9%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

1-Acetyl-3-(2-bromoethyl)-4,6-dimethylindoline (5.4 g), NaCN (3.7 g) and 18-crown-6 (480 mg) were suspended in CH3CN (50 ml), and the suspension was refluxed for 15 hr. CH3CN was evaporated under reduced pressure. CHCl3 (100 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 4.5 g of 1-acetyl-3-(2-cyanoethyl)-4,6-dimethylindoline.

Workup

  1. temperaturethe suspension was refluxed for 15 hr
  2. customCH3CN was evaporated under reduced pressure
  3. additionCHCl3 (100 ml) was added
  4. washthe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customCHCl3 was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-113b4cc5af844f29993a5183dd9959a1
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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