Nitric Acid → HCID 19867065, compound

HRID 1199519Notes

Reaction equation

HRID 1199519 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]2[CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[N+:20]([O-])([OH:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17]([N+:20]([O-:22])=[O:21])=[C:16]([CH3:18])[N:15]=[C:14]2[CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 71305Nanterinone

Product 1

HCID 19867065HCID 19867065, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 8-methyl-6-(2,4-dimethylimidazol-1-yl)-2-(1H)-quinolone (0.5 g) in concentrated sulphuric acid (4 cm3) at 0° was added concentrated nitric acid (1 cm3). The mixture was stirred for 1 hour, poured carefully onto ice (100 g), and the solution basified to pH8 with solid sodium carbonate. The resulting suspension was extracted with dichloromethane (3×100 cm3) and the combined organic phases were dried (MgSO4), filtered, and evaporated to yield a foam which was triturated with ethyl acetate/ether to afford 8-methyl-6-(2,4-dimethyl-5-nitro-imidazol-1-yl)-2-(1H)-quinolone, m.p. 244°-247°, (0.52 g).

Workup

  1. additionpoured carefully onto ice (100 g)
  2. extractionThe resulting suspension was extracted with dichloromethane (3×100 cm3)
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a foam which
  7. customwas triturated with ethyl acetate/ether

Sources & evidence

ORD record
ord-e1d19ae6cea849b8975ced0f4d5f05f5
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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