Hydrochloric Acid → Ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 606480Notes

Reaction equation

HRID 606480 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[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:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:1][C:2]2=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66768981Ethyl ((2-(aminocarbonyl)-4-fluorophenyl)amino)(oxo)acetate

Product 1

HCID 136029321Ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylateYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl ((2-(aminocarbonyl)-4-fluorophenyl)amino)(oxo)acetate (1.50 g, 5.90 mmol) in ethanol (30 mL) was added dropwise sodium ethylate (20% ethanol solution, 2.40 g, 7.08 mmol) under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was adjusted to pH 3-4 with 1N hydrochloric acid, and the precipitated insoluble material was collected by filtration. The filtered cake was washed with water and ethanol to give the title compound as a white powder (1.05 g, 75%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was collected by filtration
  3. washThe filtered cake was washed with water and ethanol

Sources & evidence

ORD record
ord-20c28bf6857e474baa1992be11b8967c
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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