Formamidine acetate → 7-Fluoroquinazolin-4(3H)-one

HRID 749178Notes

Reaction equation

HRID 749178 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].C(O)(=O)C.[CH:16](N)=[NH:17]>COCCO>[F:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:17][CH:16]=[N:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 1353984967-Fluoroquinazolin-4(3H)-oneYield 65.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

2-Amino-4-fluorobenzoic acid (15 g, 96 mmol) was dissolved in 2-methoxyethanol (97 ml). Formamidine acetate (20.13 g, 193.4 mmol) was added and the mixture heated to reflux for 18 hours. The reaction was cooled, concentrated and the residue stirred in aqueous ammonium hydroxide (0.01 N, 250 ml) for 1 hour. The suspension was filtered, washed with water and dried over phosphorus pentoxide to yield 7-fluoroquinazolin-4(3H)-one as an off-white solid (10.35 g, 65% yield):

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. filtrationThe suspension was filtered
  6. washwashed with water
  7. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-fffad5cdadf840518071761aedc95af8
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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