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

HRID 2176538Notes

Reaction equation

HRID 2176538 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-549911f2fac54bcf934695724f33d4b4
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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