Nitric Acid → HCID 178526532, compound

HRID 964997Notes

Reaction equation

HRID 964997 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].[OH-].[Na+]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 178516385quinolin-4-ol

Product 1

HCID 178526532HCID 178526532, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Hydroxyquinoline (1.45 g, 10 mmol) was dissolved in 3 ml of concentrated sulfuric acid and the solution was cooled -10° C. or less. The solution was gradually added with mixed acid (0.8 ml of concentrated nitric acid with 1.2 ml of concentrated sulfuric acid) such that the reaction solution was not elevated in temperature up to 0° C. or more, and stirred at 0° C. for 3 hours. The reaction mixture was poured into crashed ice and neutralized with 2N aqueous solution of sodium hydroxide. The resulting precipitates were filtered off and washed with water. The filtrate was combined with the washing solution and extracted with methylene chloride. After drying over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The residue was developed by silica gel column chromatography (Wako Gel™ C-200, methylene chloride : methanol=20 : 1). Firstly eluted yellow fractions were collected and the solvent was removed to obtain 380 mg (20%) of 4-hydroxy-8-nitroquinoline.

Workup

  1. temperaturethe solution was cooled -10° C. or less
  2. additionThe solution was gradually added
  3. customwas not elevated in temperature up to 0° C. or more
  4. additionThe reaction mixture was poured
  5. customThe resulting precipitates
  6. filtrationwere filtered off
  7. washwashed with water
  8. extractionextracted with methylene chloride
  9. dry with materialAfter drying over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customFirstly eluted yellow fractions were collected
  12. customthe solvent was removed

Sources & evidence

ORD record
ord-fdb7d48e09134c2bbe2ad2511afcb8fd
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

Loading…