Nitric Acid → HCID 20068746, compound

HRID 981906Notes

Reaction equation

HRID 981906 reaction equation
[CH2:1]([N:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[N:15]([CH3:18])[CH:16]=[N:17][C:7]=2[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[N+:20]([O-])([OH:22])=[O:21]>S(=O)(=O)(O)O>[CH2:1]([N:5]1[C:14]2[CH:13]=[CH:12][C:11]([N+:20]([O-:22])=[O:21])=[CH:10][C:9]=2[C:8]2[N:15]([CH3:18])[CH:16]=[N:17][C:7]=2[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 30770174H-Imidazo(4,5-c)quinolin-4-one, 1,5-dihydro-5-butyl-1-methyl-

Product 1

HCID 20068746HCID 20068746, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 100 mg (0.39 mmol) of Compound 1 obtained in Example 1 in 0.13 ml of sulfuric acid was added dropwise to an acid mixture consisting of 0.045 ml of 61% nitric acid and 0.35 ml of 96% sulfuric acid with ice cooling, followed by stirring for 30 minutes. After neutralization with an aqueous 50% sodium hydroxide, the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=10/1) to afford 13 mg of Compound 14.

Workup

  1. extractionAfter neutralization with an aqueous 50% sodium hydroxide, the mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (eluting solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-7ff34ef174b84a5da9cd014b6302aa69
Source dataset
uspto-grants-1991_02
Patent number
US04994468

Reaction notes

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