Nitric Acid → 5-Chloro-6-nitro-2,4(1H,3H)-quinazolinedione

HRID 1760740Notes

Reaction equation

HRID 1760740 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][C:6](=[O:12])[NH:7]2.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[Cl:1][C:2]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][C:6](=[O:12])[NH:7]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 3340215-Chloroquinazoline-2,4-diol

Product 1

HCID 217868715-Chloro-6-nitro-2,4(1H,3H)-quinazolinedione

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of the above quinazolinedione (0.98 g, 5.0 mmol) in conc. H2SO4 (5 mL) was cooled to −10° C., and 90% HNO3 (0.35 g, 5.0 mmol) was added with stirring. Stirring continued for 1 h at −10° C., and 1.5 h at room temperature. The mixture was poured onto ice, filtered, washed with water and dried to give 5-chloro-6-nitroquinazolin-2,4-dione, along with some of the 8-nitro isomer (1.3 g, 94%).

Workup

  1. stirringStirring
  2. custom1.5 h
  3. customat room temperature
  4. additionThe mixture was poured onto ice
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d9cfadb4fd0445f2a56b8d94edd7c5aa
Source dataset
uspto-grants-2005_01
Patent number
US06844435B2

Reaction notes

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