Indole → 3-(Cyanoacetyl)indole

HRID 1695230Notes

Reaction equation

HRID 1695230 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1>C(OC(=O)C)(=O)C>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:4](=[O:6])[CH2:3][C:1]#[N:2])=[CH:8]1

Participants

4

Reactant 2

HCID 798IndoleHCID 9740Cyanoacetic acid

Product 1

HCID 24535683-(Cyanoacetyl)indoleYield 85%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
50 °C

Procedure

In a flask, cyanoacetic acid (5.0 g, 58.8 mmol, 1.2 eq) was dissolved in acetic anhydride (50 mL) and heated at 50° C. Indole (5.8 g, 50.0 mmol, 1.0 eq) was added and the reaction was heated at 80° C. for 5 min. A white precipitate crushed out of the solution; the reaction was cooled to room temperature and then filtered. The solid obtained (620.0 mg, 85% yield) was used for the next step without further purification.

Workup

  1. temperaturethe reaction was heated at 80° C. for 5 min
  2. customA white precipitate crushed out of the solution
  3. temperaturethe reaction was cooled to room temperature
  4. filtrationfiltered
  5. customThe solid obtained (620.0 mg, 85% yield)
  6. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-94103ea2bc624d798b5d2d522e6133b0
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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