Formamide → 7-Fluoroquinazolin-4(3H)-one

HRID 75707

Reaction equation

HRID 75707 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:12]([NH2:14])=O>CN(C)C=O>[F:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:14][CH:12]=[N:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 1353984967-Fluoroquinazolin-4(3H)-oneYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

2-amino-4-fluorobenzoic acid (100 g, 0.64 mol) and formamide (154 mL, 3.87 mol) were mixed with a catalytic amount (1 mL) of N,N-dimethylformamide. The mixture was heated to 180° C. and further stirred for 14 hours. The mixture was cooled to room temperature, and distilled water (1000 mL) was added thereto. The mixture was stirred for 30 min and filtered to obtain the title compound (86 g, 81.3%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. distillationdistilled water (1000 mL)
  3. additionwas added
  4. stirringThe mixture was stirred for 30 min
  5. filtrationfiltered

Sources & evidence

ORD record
ord-25bcd9b5e8a44c889d87d8e953462ed9
Source dataset
uspto-grants-2014_09
Patent number
US08835458B2

Linked notes

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