Phosphorus oxychloride → 3-Chloroquinoxaline-6-carbonitrile

HRID 2279409Notes

Reaction equation

HRID 2279409 reaction equation
O=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[N:4]=[CH:3]1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]#[N:13])=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 451217293-Hydroxyquinoxaline-6-carbonitrile

Product 1

HCID 738939393-Chloroquinoxaline-6-carbonitrileYield 79.4%

Procedure

A solution of 3-oxo-3,4-dihydro-quinoxaline-6-carbonitrile (5.99 g, 35 mmol, 1.0 eq) in phosphorus oxychloride (26 mL, 280 mmol, 8.0 eq) is heated under reflux for 1 hour. Then the reaction mixture is cooled down to room temperature and the solvent is evaporated. The residue is poured into ice water, the resulting mixture is neutralized with sodium carbonate and extracted with ethyl acetate (3×50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane 100%) to afford 3-chloro-quinoxaline-6-carbonitrile as a white solid (5.27 g, 79% yield).

Workup

  1. temperatureunder reflux for 1 hour
  2. customthe solvent is evaporated
  3. additionThe residue is poured into ice water
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude product that
  9. customis purified by column chromatography (silica gel, eluent: dichloromethane 100%)

Sources & evidence

ORD record
ord-2acbd7c6ed23404c8b25d818aea51fc9
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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