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

HRID 1723715Notes

Reaction equation

HRID 1723715 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].C(=O)(O)[O-].[Na+]>O>[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

5

Reactant 3

HCID 160693Formamidine acetateHCID 516892Sodium BicarbonateHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 1353984967-Fluoroquinazolin-4(3H)-oneYield 91.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

A heterogeneous mixture of 2-amino-4-fluorobenzoic acid (8.7 g, 56 mmol) and formamidine acetate (29.2 g, 280 mmol) was stirred and heated at 165° C. for 2 h. The reaction mixture was suspended in H2O and the mixture was carefully basified with saturated sodium bicarbonate solution followed by stirring for 1 h. The brown solid was collected by filtration, washed with H2O and air dried to afford 8.42 g (91%) of 7-fluoroquinazolin-4(3H)-one. MS 165.0 (ES+).

Workup

  1. stirringby stirring for 1 h
  2. filtrationThe brown solid was collected by filtration
  3. washwashed with H2O and air
  4. customdried

Sources & evidence

ORD record
ord-24135adbfceb44b3a988c1f29d741aea
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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