Hydrochloric Acid → 2-Iodo-3-phenylquinoxaline

HRID 44436Notes

Reaction equation

HRID 44436 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[I-:19].[Na+].C(#N)C>C1COCC1.CCOCC.CCCCCC>[I:19][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6774642-Chloro-3-phenylquinoxaline

Product 1

HCID 866386272-Iodo-3-phenylquinoxalineYield 95%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To the 2-chloro-3-phenylquinoxaline (4.15 mmol) in dry THF (10 ml) was added a solution of 2 M HCl in ether (4 ml). After 5 minutes the solvents were removed by vacuum. Dry sodium iodide (41.5 mmol) and acetonitrile (30 ml) were added to the hydrochloride salt and refluxed for 5 hrs. The reaction was quenched by the addition of an aqueous solution of 10% K2CO3 and 5% NaHSO3 (15 ml). After extraction with dichloromethane, and drying the combined organic layers over MgSO4 the solvents were evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography with (1:10) EtOAc:hexane, to give 95% yield of the desired product.

Workup

  1. customAfter 5 minutes the solvents were removed by vacuum
  2. temperaturerefluxed for 5 hrs
  3. customThe reaction was quenched by the addition of an aqueous solution of 10% K2CO3 and 5% NaHSO3 (15 ml)
  4. extractionAfter extraction with dichloromethane
  5. dry with materialdrying the combined organic layers over MgSO4 the solvents
  6. customwere evaporated under reduced pressure
  7. customThe resulting crude product was purified by silica gel chromatography with (1:10) EtOAc

Sources & evidence

ORD record
ord-25281a695168484dad696d7729c733c2
Source dataset
uspto-grants-2013_09
Patent number
US08541428B2

Reaction notes

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