Carbon Dioxide → 2-Adamantyl-6-methoxy-8-nitroquinoline

HRID 489920Notes

Reaction equation

HRID 489920 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[C:16]12(C(O)=O)[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.OS(O)(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].C(=O)=O.[NH4+].[OH-]>CC#N.O.[N+]([O-])([O-])=O.[Ag+]>[CH:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH:17]1[C:8]1[CH:7]=[CH:6][C:5]3[C:10](=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=1)[CH2:23]2

Participants

10

Reactant 6

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 68226-Methoxy-8-nitroquinolineHCID 132351-Adamantanecarboxylic acidHCID 14923Ammonium HydroxideHCID 62648Ammonium Persulfate

Product 1

HCID 222630102-Adamantyl-6-methoxy-8-nitroquinolineYield 70%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

6-Methoxy-8-nitroquinoline (1 mmol) (scheme 1) was dissolved in CH3CN (5 mL) while reaction mixture was warmed to 70° C. Silver nitrate (0.6 mmol), 1-adamantanecarboxylic acid (2 mmol), and 10% H2SO4 (10 mL) was then added to the reaction mixture. A freshly prepared solution of ammonium persulfate (3 mmol) in water (10 mL) was added drop wise to the pre-heated (70° C.) mixture during 10 minutes. The heating source was then removed and reaction proceeded with evolution of carbon dioxide. After 10 minutes, reaction mixture was poured onto ice, and resulting mixture was made alkaline with addition of 30% NH4OH. Extracted with ethyl acetate (4×50 mL), and combined extracts were washed with NaCl solution (2×10 mL). Dried over Na2SO4 and solvent removed in vacuo to afford oil, which on flash column chromatography over silica gel (230-400 mesh) gave 2-adamantyl-6-methoxy-8-nitroquinoline in good yield.

Workup

  1. customwhile reaction mixture
  2. temperaturepre-heated (70° C.) mixture during 10 minutes
  3. customThe heating source was then removed
  4. customreaction
  5. customreaction mixture
  6. additionwas poured onto ice
  7. customresulting mixture
  8. extractionExtracted with ethyl acetate (4×50 mL)
  9. washwere washed with NaCl solution (2×10 mL)
  10. dry with materialDried over Na2SO4 and solvent
  11. customremoved in vacuo
  12. customto afford oil, which on flash column chromatography over silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-1c2628c4685d4714923ea211f9ed1d67
Source dataset
uspto-grants-2005_12
Patent number
US06979740B2

Reaction notes

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