5-Bromoisatoic Anhydride → 6-bromoquinazolin-4-ol

HRID 219129Notes

Reaction equation

HRID 219129 reaction equation
[Br:1][C:2]1[CH:13]=[C:6]2[C:7](O[C:10](=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].C([O-])(=O)C.C(N)=[NH2+:19]>CC(O)C>[Br:1][C:2]1[CH:13]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:10][NH:19][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 2885615-Bromoisatoic AnhydrideHCID 10285782Iminomethanaminium acetate

Product 1

HCID 1354449056-bromoquinazolin-4-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5-bromoisatoic anhydride (5.0 g, 21 mmol) and formamidinium acetate (2.2 g, 21 mmol) in 60 mL of i-PrOH was heated at reflux for 10 hours. The reaction mixture was cooled to rt and the white solid was collected by filtration. The white solid was washed with small amount of i-PrOH and dried in air to give desired product 6-bromoquinazolin-4(3H)-one. MS (ESI, pos. ion) m/z: 224.9 (M+1).

Workup

  1. temperatureat reflux for 10 hours
  2. filtrationthe white solid was collected by filtration
  3. washThe white solid was washed with small amount of i-PrOH
  4. customdried in air

Sources & evidence

ORD record
ord-638eb79c0919478f92004a860c9e5382
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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