Nitric Acid → 6-bromo-7-methyl-8-nitroquinazolin-4(3H)-one

HRID 2092307Notes

Reaction equation

HRID 2092307 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[N:13]=[CH:12][NH:11][C:10]2=[O:18].[N+:19]([O-])([OH:21])=[O:20]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[CH3:17])[N:13]=[CH:12][NH:11][C:10]2=[O:18]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1357422976-bromo-7-methylquinazolin-4(3H)-one

Product 1

HCID 1358945796-bromo-7-methyl-8-nitroquinazolin-4(3H)-one

Procedure

To H2SO4 (98%, 15 ml) was added 6-bromo-7-methylquinazolin-4(3H)-one (1.0 g, 4.2 mmol) and the mixture was stirred at rt until dissolution was complete. The mixture was cooled to 0° C. and then nitric acid (fuming) (0.26 g, 4.2 mmol) was added dropwise at 0° C. and stirred for 10 min, and then stirred at rt for 5 h. The mixture was poured onto ice (300 g) and extracted with EtOAc (3×80 ml). The combined organic layers were washed with brine (100 ml), dried over MgSO4 and concentated in vacuo. The product was recrystalized from MeOH (˜15 ml). MS (M+H)+ 284, 286.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringstirred for 10 min
  3. stirringstirred at rt for 5 h
  4. additionThe mixture was poured onto ice (300 g)
  5. extractionextracted with EtOAc (3×80 ml)
  6. washThe combined organic layers were washed with brine (100 ml)
  7. dry with materialdried over MgSO4
  8. customThe product was recrystalized from MeOH (˜15 ml)

Sources & evidence

ORD record
ord-9579679b426145cea12da08d5e2cd8e3
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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