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

HRID 1592942Notes

Reaction equation

HRID 1592942 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1>O>[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[N+:6]([O-:9])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 1357386737-Bromo-6-nitroquinazolin-4(3H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of concentrated sulfuric acid (3 mL) and fuming nitric acid (3 mL) was added 7-bromo-3H-quinazolin-4-one (1.67 g, 7.42 mmol), and the mixture was heated at an oil bath temperature of 95° C. to 100° C. for 1 hr. The reaction mixture was poured into water (50 mL), and the product was collected by filtration, washed with water and dried under reduced pressure to give an about 5.6:1 mixture (1.3 g, 65%) of the objective 7-bromo-6-nitro-3H-quinazolin-4-one and 7-bromo-8-nitro-3H-quinazolin-4-one.

Workup

  1. temperaturethe mixture was heated at an oil bath temperature of 95° C. to 100° C. for 1 hr
  2. filtrationthe product was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8ccccbfae46e473680178c470e93fad3
Source dataset
uspto-grants-2007_11
Patent number
US07294629B2

Reaction notes

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