Ammonia → 6-fluoroquinazolin-4-ol

HRID 273777Notes

Reaction equation

HRID 273777 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2O[C:9](=O)[NH:8][C:7](=[O:12])[C:6]=2[CH:13]=1.[NH3:14]>C(N)=O>[F:1][C:2]1[CH:13]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:14]=[CH:9][NH:8][C:7]2=[O:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 200941616-Fluoro-2H-1,3-benzoxazine-2,4(3H)-dione

Product 1

HCID 1354805206-fluoroquinazolin-4-ol

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

1. 3.62 g of 6-fluoro-2H-1,3-benzoxazine-2,4(1H)-dione are suspended in 15 ml of formamide. Gaseous ammonia is introduced while stirring during about 10 min. until the suspension is saturated and the mixture is stirred at room temperature for a further 1 h. Subsequently, the mixture is stirred at 125° C. (bath temperature) for 16 h. The solvent is then distilled off in a high vacuum. The residue is triturated in 50 ml of water and then cooled slightly. The resulting crystals are filtered off, washed with ice-cold water and dried over calcium chloride in a vacuum. 2.9 g of crude 6-fluoro-3H-quinazoline-4-one are obtained. The substance melts at 252°-255° C. after recrystallization from ethyl acetate.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 1 h
  2. stirringSubsequently, the mixture is stirred at 125° C. (bath temperature) for 16 h
  3. distillationThe solvent is then distilled off in a high vacuum
  4. customThe residue is triturated in 50 ml of water
  5. temperaturecooled slightly
  6. filtrationThe resulting crystals are filtered off
  7. washwashed with ice-cold water
  8. dry with materialdried over calcium chloride in a vacuum

Sources & evidence

ORD record
ord-c8ade91d1bb14dda9d2126ec2d97e8f2
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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