Nitric Acid → 7-Bromo-6-nitroquinazolin-4(3H)-one

HRID 1528031Notes

Reaction equation

HRID 1528031 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 1357386737-Bromo-6-nitroquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 7-bromo-4-quinazolinone (2.6 g) in 5 mL of concentrated H2SO4 and 5 mL of fuming HNO3 was heated at 100° C. for 1 h. After the reaction was cooled to room temperature, the mixture was poured into ice-water. The solid was collected via filtration, and used without further purification, 7-bromo-6-nitro-4-quinazolinone (mixed with 7-bromo-8-nitro-4-quinazolinone, LCMS ESI(+) m/z: 270/271 (M+1).

Workup

  1. filtrationThe solid was collected via filtration
  2. customused without further purification, 7-bromo-6-nitro-4-quinazolinone (
  3. additionmixed with 7-bromo-8-nitro-4-quinazolinone, LCMS ESI(+) m/z

Sources & evidence

ORD record
ord-6195a4384e064dada86a13d6fa6edce0
Source dataset
uspto-grants-2015_07
Patent number
US09090588B2

Reaction notes

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