Indole → 3-(Cyanoacetyl)indole

HRID 1370082Notes

Reaction equation

HRID 1370082 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([CH2:12][C:13]([O-])=[O:14])#[N:11].[K+].CS(Cl)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:10]([CH2:12][C:13]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:14])#[N:11]

Participants

6

Reactant 4

HCID 798IndoleHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 23664620Potassium 2-cyanoacetate

Product 1

HCID 24535683-(Cyanoacetyl)indole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(Cyanoacetyl)indole was prepared by suspending indole (11.71 g, 0.10 mmol) and potassium cyanoacetate (24.6 g, 0.2 mmol) in acetonitrile (300 mL), and to this methanesulphonylchloride (7.7 mL, 0.1 mmol) was added. The resulting mixture was stirred at ambient temperature for 1 h, and then sodium carbonate (10 g in 50 mL water) was added. After 5 min, the organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was recrystallised from ethanol (100 mL) to give the desired material as an orange solid (4.31 g), m.p. 226-227°. δH (d6 DMSO) 12.20 (1H, bs), 8.38 (1H, d, J 2.8 Hz), 8.14-8.10 (1H, m), 7.53-7.50 (1H, m), 7.25-7.21 (2H, m) and 4.49 (2H, s).

Workup

  1. waitAfter 5 min
  2. customthe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallised from ethanol (100 mL)

Sources & evidence

ORD record
ord-6625e90a6dbb46d88cd1326508183659
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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