Hydrochloric Acid → Ethyl 5-methyl-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 606495Notes

Reaction equation

HRID 606495 reaction equation
[NH2:1][C:2]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:3].CC[O-].[Na+].Cl>C(O)C>[CH3:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:2](=[O:3])[NH:1][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66768983Ethyl ((2-(aminocarbonyl)-3-methylphenyl)amino)(oxo)acetate

Product 1

HCID 136029326Ethyl 5-methyl-4-oxo-3,4-dihydroquinazoline-2-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl ((2-(aminocarbonyl)-3-methylphenyl)amino)(oxo)acetate (760 mg, 3.04 mmol) in ethanol (15 mL) was added dropwise sodium ethylate (20% ethanol solution, 1.14 g, 3.34 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 1N Hydrochloric acid (5 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was suspended in diisopropyl ether-ethanol, and the insoluble material was collected by filtration to give the title compound as a white powder (450 mg, 64%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe insoluble material was collected by filtration

Sources & evidence

ORD record
ord-5a3f68c73d6243ca89356bde917f3824
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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