Nitric Acid → 2,8-Dimethyl-5-nitro-4H-1-benzopyran-4-one

HRID 1669775Notes

Reaction equation

HRID 1669775 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:13].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=[CH:6][C:5]=2[CH3:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 11355780HCID 11355780, compound

Product 1

HCID 574388902,8-Dimethyl-5-nitro-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2 g (11.48 mmol) of 2,8-dimethyl-4H-chromen-4-one are dissolved in 15 ml of concentrated sulfuric acid and, at 0° C., 0.7 g (11.48 mmol) of fuming nitric acid is added, during which the temperature should not exceed 5° C. The mixture is then stirred at room temperature for 1 h. The reaction mixture is poured into ice-water, whereupon a colorless solid precipitates. This is filtered off and washed several times with water and ice-cold methanol. 2.3 g (90.8% of theory) of the title compound are obtained.

Workup

  1. customexceed 5° C
  2. customprecipitates
  3. filtrationThis is filtered off
  4. washwashed several times with water and ice-cold methanol

Sources & evidence

ORD record
ord-697a226a7dcb423294a972ac35587375
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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