Citric Acid → Ethyl 6-amino-4-oxo-3,4-dihydro-2-quinazolinecarboxylate

HRID 606492Notes

Reaction equation

HRID 606492 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([C:16]([NH2:18])=[O:17])[CH:3]=1.C1COCC1.CC[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:18][C:16]2=[O:17]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 2723922Sodium ethoxideHCID 66769061Ethyl {[4-amino-2-(aminocarbonyl)phenyl]amino}(oxo)acetate

Product 1

HCID 136054462Ethyl 6-amino-4-oxo-3,4-dihydro-2-quinazolinecarboxylateYield 40.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl {[4-amino-2-(aminocarbonyl)phenyl]amino}(oxo)acetate (1.96 g) in a mixed solvent of THF (60 ml)-ethanol (30 mL) was added dropwise sodium ethylate (20% ethanol solution, 2.82 g), and the mixture was stirred at room temperature for 12 hr. 10% Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated, and the obtained crude crystals were washed with diisopropyl ether to give the title compound (738 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe obtained crude crystals
  5. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-fa8d502dcf6842908625bd78cd5d047a
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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