Nitric Acid → 5-bromo-7-methyl-8-nitroquinazolin-4(3H)-one

HRID 1469760Notes

Reaction equation

HRID 1469760 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][CH:6]=[N:7]2.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1363368235-bromo-7-methylquinazolin-4(3H)-one

Product 1

HCID 1363368225-bromo-7-methyl-8-nitroquinazolin-4(3H)-oneYield 59.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-bromo-7-methylquinazolin-4(3H)-one (700 mg, 2.94 mmol) in cone. H2SO4 (10 mL) was added fuming HNO3 (185 μL, 2.94 mmol) at 0° C. and then the reaction mixture was stirred at rt for 12 h. Then the reaction mixture was quenched with water and the precipitate obtained was filtered and dried to afford 500 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 12.80 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 2.41 (s, 3H).

Workup

  1. customThen the reaction mixture was quenched with water
  2. customthe precipitate obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-a2efc1c9c79b4a37b1135d8024f063d1
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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