Toluene → HCID 135742588, compound

HRID 468557Notes

Reaction equation

HRID 468557 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[CH:15]=[N:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16]C)[CH:12]=2)[N:7]=1.C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>O>[Cl:5][C:6]1[CH:15]=[N:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 126864122-Chloro-6-methoxyquinoxalineHCID 21226206Ethyl acetate hexane

Product 1

HCID 135742588HCID 135742588, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aluminium trichloride (85 mg, 638 μmol) was added as a single portion to a stirred mixture of 2-chloro-6-methoxyquinoxaline (73 mg, 375 μmol) and anhydrous toluene (3 ml) under an Argon atmosphere. The reaction mixture was heated at reflux for approx. 1 hr, then allowed to stir overnight at room temperature. Tlc (silica; 2:1 hexane/ethyl acetate) showed no remaining starting material and new polar material. Water (1 ml) and ice were added and the mixture stirred. The contents were partitioned between water (5 ml) and ethyl acetate (100 ml). The aqueous phase was extracted into ethyl acetate (50 ml), then the organic extracts combined and washed with water (10 ml), followed by brine (10 ml) and dried (Na2SO4). Concentration gave a brown solid, which was pre-adsorbed onto silica, then chromatographed on silica (9 g); eluent: 20% ethyl acetate in hexane then 25% ethyl acetate in hexane to give 2-chloro-6-hydroxyquinoxaline 54 mg (79%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for approx. 1 hr
  3. stirringthe mixture stirred
  4. customThe contents were partitioned between water (5 ml) and ethyl acetate (100 ml)
  5. extractionThe aqueous phase was extracted into ethyl acetate (50 ml)
  6. washwashed with water (10 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationConcentration
  9. customgave a brown solid, which
  10. customchromatographed on silica (9 g)

Sources & evidence

ORD record
ord-786ec07ae1224cae8a84ea78f1b7de0d
Source dataset
uspto-grants-2014_01
Patent number
US08624025B2

Reaction notes

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