Hexane → HCID 86662010, compound

HRID 1422823Notes

Reaction equation

HRID 1422823 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:6]([N:7]=[CH:8][C:9](=O)[NH:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:18])=O.CCCCCC>C(OCC)(=O)C>[Cl:18][C:9]1[CH:8]=[N:7][C:6]2[C:11](=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 66746556HCID 66746556, compound

Product 1

HCID 86662010HCID 86662010, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7,8-dimethoxy-quinoxalin-2-one (5.0 g, 24.25 mmol, 1.0 eq) in phosphorus oxychloride (25 mL, 268.21 mmol, 11.06 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 saturated sodium hydrogen 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: hexane:ethyl acetate, 2:1 to 1:1, v/v) to afford 2-chloro-7,8-dimethoxy-quinoxaline as a light yellow solid (4.2 g, 77% 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

Sources & evidence

ORD record
ord-eff4e6b88f284d74b7d5ed19c69d1a7d
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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