Ethyl cyanoformate → Ethyl 5,6-difluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 606493Notes

Reaction equation

HRID 606493 reaction equation
Cl.[F:2][C:3]1[C:13]([F:14])=[C:7]([C:8]([O:10]CC)=O)[C:6]([NH2:15])=[CH:5][CH:4]=1.[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:17]>Cl.C(O)(=O)C>[F:14][C:13]1[C:3]([F:2])=[CH:4][CH:5]=[C:6]2[C:7]=1[C:8](=[O:10])[NH:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:15]2

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 66768485Ethyl 6-amino-2,3-difluorobenzoate hydrochloride

Product 1

HCID 136029322Ethyl 5,6-difluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 22641269Acetate-hydrochloric acidSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 5,6-difluoroanthranilate hydrochloride (2.50 g, 10.5 mmol) was suspended in 1N hydrogen chloride-acetic acid solution (50 mL), ethyl cyanoformate (1.14 g, 11.6 mmol) was added thereto, and the mixture was stirred under heating at 80° C. for 3 hr. The reaction mixture allowed to cool to room temperature, and concentrated under reduced pressure. The residue was suspended in ethanol, and the insoluble material was collected by filtration to give the title compound as a white powder (2.18 g, 82%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. filtrationthe insoluble material was collected by filtration

Sources & evidence

ORD record
ord-e10b5da21dd94dfa8c525df5b61e8e3c
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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