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

HRID 606497Notes

Reaction equation

HRID 606497 reaction equation
[NH2:1][C:2]([C:4]1[C:9]([F: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>[F: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 66769038Ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate

Product 1

HCID 136029330Ethyl 5-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate (2.45 g, 9.64 mmol) in ethanol (50 mL) was added dropwise sodium ethylate (20% ethanol solution, 3.61 g, 10.6 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid (20 mL) was added to the reaction mixture, and the insoluble material was collected by filtration. The solid was washed with water and diethyl ether to give the title compound as a pale-yellow powder (1.29 g, 57%).

Workup

  1. temperaturecooling
  2. filtrationthe insoluble material was collected by filtration
  3. washThe solid was washed with water and diethyl ether

Sources & evidence

ORD record
ord-a8f50e6d152243fe97da32acd2f56dad
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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