Ethyl Acrylate → HCID 67025240, compound

HRID 1512809Notes

Reaction equation

HRID 1512809 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>ClCCCl.C(Cl)Cl>[C:10]([C:7]1[CH:8]=[C:9]2[C:4]([C:3]([CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:2][NH:1]2)=[CH:5][CH:6]=1)#[N:11]

Participants

5

Reactant 2

HCID 8821Ethyl AcrylateHCID 851461H-indole-6-carbonitrile

Product 1

HCID 67025240HCID 67025240, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

1H-indole-6-carbonitrile (D12) (3.2 g), ferric chloride (3.7 g) and ethyl acrylate (7.3 mL) in DCE (7 mL) was added to a sealed tube. The tube was sealed, and the reaction mixture was stirred at 120° C. for 2 hours. After cooling, the reaction mixture was diluted with DCM. The organic layer was washed with 0.5 M HCl, brine, dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography (20% EtOAc in hexane) to afford ethyl 3-(6-cyano-1H-indol-3-yl)propanoate (D106) (3.1 g) as a yellow solid. δH (CDCl3, 400 MHz): 1.24 (3H, t), 2.71 (2H, t), 3.11 (2H, t), 4.14 (2H, q), 7.24 (1H, dd), 7.36 (1H, dd), 7.67 (1H, d), 7.70 (1H, dd), 8.36 (1H, br s). MS (ES): C14H14N2O2 requires 242. found 243.1 (M+H+).

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling
  3. washThe organic layer was washed with 0.5 M HCl, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried solution was concentrated
  6. customThe residue was purified by column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-d189b87b85a44a1aaf4e3537f0eb4112
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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