2,4-Dichloro-5,8-dimethoxyquinoline → HCID 22646491, compound

HRID 393522Notes

Reaction equation

HRID 393522 reaction equation
[N+]([O-])([O-])=O.[NH4+].[Ce].[Cl:7][C:8]1[CH:17]=[C:16]([Cl:18])[C:15]2[C:10](=[C:11]([O:21]C)[CH:12]=[CH:13][C:14]=2[O:19]C)[N:9]=1>CC#N.O>[Cl:7][C:8]1[CH:17]=[C:16]([Cl:18])[C:15]2[C:14](=[O:19])[CH:13]=[CH:12][C:11](=[O:21])[C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 123256172,4-Dichloro-5,8-dimethoxyquinolineHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 22646491HCID 22646491, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Cerium ammonium nitrate (CAN 21.4 g, 39.03 mmol) is added portionwise to a solution of 2,4-dichloro-5,8-dimethoxyquinoline (2.85 g, 11.04 mmol) in a CH3CN/H2O mixture (150 ml/75 ml). The reaction mixture is stirred at ambient temperature for 40 min. The acetonitrile is subsequently evaporated and 50 ml of water and 200 ml of a saturated NaHCO3 solution are added. The aqueous phase is extracted with CH2Cl2 (5 times 200 ml). After drying over MgSO4, the solvent is evaporated on a rotary evaporator to give the expected compound in the form of a brown powder (1.9 g).

Workup

  1. customThe acetonitrile is subsequently evaporated
  2. addition50 ml of water and 200 ml of a saturated NaHCO3 solution are added
  3. extractionThe aqueous phase is extracted with CH2Cl2 (5 times 200 ml)
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent is evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-8162fe6e2d37474c8793a84b3f8b5dd7
Source dataset
uspto-grants-2004_10
Patent number
US06809096B1

Reaction notes

Loading…