Ethyl 5,8-dimethoxyquinoline-3-carboxylate → HCID 11053454, compound

HRID 1370326Notes

Reaction equation

HRID 1370326 reaction equation
[N+]([O-])([O-])=O.[NH4+].[Ce].C[O:8][C:9]1[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]2[C:10]=1[CH:11]=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:13]=[N:14]2>CC#N.O>[O:8]=[C:9]1[CH:18]=[CH:17][C:16](=[O:19])[C:15]2[N:14]=[CH:13][C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][C:10]1=2

Participants

4

Reactant 2

HCID 18511056Ethyl 5,8-dimethoxyquinoline-3-carboxylateHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 11053454HCID 11053454, compoundYield 91%

Reagents, catalysts & solvents 1

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

Procedure

7.4 g of cerium ammonium nitrate are added at ambient temperature to a solution of 1 g (3.83 mmol) of ethyl 5,8-dimethoxyquinoline-3-carboxylate in a CH3CN/H2O mixture (45 mL/23 mL). The reaction medium is stirred for 1 hour and the acetonitrile is then evaporated off. The medium is basified by adding 17 mL of saturated NaHCO3 solution. 60 mL of H2O are added and this mixture is then extracted with CH2Cl2 (3 times 100 mL). After drying over MgSO4 and evaporating off the solvent, 0.8 g of ethyl 5,8-dioxoquinoline-3-carboxylate is obtained.

Workup

  1. customthe acetonitrile is then evaporated off
  2. additionby adding 17 mL of saturated NaHCO3 solution
  3. addition60 mL of H2O are added
  4. extractionthis mixture is then extracted with CH2Cl2 (3 times 100 mL)
  5. dry with materialAfter drying over MgSO4
  6. customevaporating off the solvent

Sources & evidence

ORD record
ord-d1a23f45069141e09a7f8ce9ab8d14ae
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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