Formamide → 6-bromoquinazolin-4-ol

HRID 1626323Notes

Reaction equation

HRID 1626323 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:12]([NH2:14])=O>CCO>[Br:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:12][NH:14][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 713FormamideHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 1354449056-bromoquinazolin-4-olYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Briefly, 2-amino-5-bromobenzoic acid (A, 50.0 g, 0.233 mmol, 1.0 equiv) is added to formamide (50.0 mL, d=1.133, 56.7 g, 1.26 mmol). The reaction mixture is heated at reflux for 12 h. The solution is then cooled to 70° C., and EtOH (100 mL) is added to the reaction mixture. The resultant precipitates are collected by filtration, washed with EtOH (50 mL), and dried under vacuum to provide the desired 6-bromo-3H-quinazolin-4-one (B, 42.5 g, 0.189 mol) in 81% yield: ESI-MS m/z 225.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 12 h
  3. customThe resultant precipitates
  4. filtrationare collected by filtration
  5. washwashed with EtOH (50 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-93e4a53ed97a49268d67efdd5ff8ecba
Source dataset
uspto-grants-2014_07
Patent number
US08785459B2

Reaction notes

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