Acrylonitrile → 6-chloro-2H-chromene-3-carbonitrile

HRID 1715341Notes

Reaction equation

HRID 1715341 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11](#[N:14])[CH:12]=[CH2:13].C1N2CCN(CC2)C1>CCOCC>[Cl:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:10][CH2:13][C:12]([C:11]#[N:14])=[CH:7]2

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 14759206-chloro-2H-chromene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-chloro-2-hydroxy-benzaldehyde Compound 15a (10.0 mmol, 1.7 g), acrylonitrile (50.0 mmol, 2.14 mL) and DABCO (2.33 mmol, 0.26 g) were mixed together and heated to reflux overnight using an oil bath. After the flask was cooled to room temperature, Et2O (100 mL) was added and the Et2O layer was washed with 10% NaOH solution followed by 1N HCl and brine. The organic layer was dried over MgSO4, filtered and the solvent was removed in vacuo to obtain 6-chloro-2H-chromene-3-carbonitrile Compound 15b as a yellow solid (1.42 g, 74%), which was used in the next step without further purification (the preceding was described in Wise, L. et al. J. Med. Chem., 1988, 31, 688).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. washthe Et2O layer was washed with 10% NaOH solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e79bc47ab3384ad09c201c43a75389e1
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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