Nitric Acid → HCID 135813639, compound

HRID 1760745Notes

Reaction equation

HRID 1760745 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:12])[NH:5][CH:6]=[N:7]2.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Cl:1][C:2]1[C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:12])[NH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1354299165-Chloroquinazolin-4(1H)-one

Product 1

HCID 135813639HCID 135813639, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of the above quinazolinone (1.26 g, 7.0 mmol) in conc. H2SO4 (7 mL) was cooled to −20° C., and 90% HNO3 (0.49 g, 7.0 mmol) was added with stirring. Stirring continued for 1 h at −20° C., and 2 h at room temperature. The mixture was poured onto ice, filtered, washed with water and dried to give 5-chloro-6-nitroquinazolin-4-one, along with the 8-nitro isomer in a 4:1 ratio. Three recrystallizations from EtOH gave the product as a 6:1 ratio of isomers (0.85 g).

Workup

  1. stirringStirring
  2. custom2 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-9f1569f8912243baa87d8dcc005bd88f
Source dataset
uspto-grants-2005_01
Patent number
US06844435B2

Reaction notes

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