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

HRID 81454

Reaction equation

HRID 81454 reaction equation
[CH3:1][N-:2]C.[NH2:4][C:5]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8].C(N)=O>O>[F:14][C:12]1[CH:13]=[C:5]2[C:6]([C:7](=[O:8])[NH:2][CH:1]=[N:4]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 182180DimethylazanideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 1353984967-Fluoroquinazolin-4(3H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A catalytic amount (1 ml) of N,N-dimethylamide was added to 2-amino-4-fluorobenzoic acid (50 g, 322 mmol) and formamide (77 ml, 1934 mmol), and the resulting solution was stirred. The solution was heated to 180° C. and stirred for 14 hours. The temperature of the solution was cooled to room temperature, and 300 ml of distilled water was added thereto. The resulting solid was stirred about 30 min, and filtered to obtain the title compound 41.3 g (yield: 78%).

Workup

  1. stirringstirred for 14 hours
  2. temperatureThe temperature of the solution was cooled to room temperature
  3. stirringThe resulting solid was stirred about 30 min
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c6d31f2832c24e03bae54d8181808b82
Source dataset
uspto-grants-2014_09
Patent number
US08846699B2

Linked notes

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