Sodium Bicarbonate → 2-(2-Azabicyclo[2.2.2]oct-2-yl)-6-nitroquinoline

HRID 6799Notes

Reaction equation

HRID 6799 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:26]12[CH2:33][CH2:32][CH:29]([CH2:30][CH2:31]1)[CH2:28][NH:27]2.C(=O)(O)[O-].[Na+]>C(O)C>[CH:26]12[CH2:33][CH2:32][CH:29]([CH2:30][CH2:31]1)[CH2:28][N:27]2[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 109217232-Chloro-6-nitroquinolineHCID 114033482-Azabicyclo[2.2.2]octane p-toluenesulfonic acid salt

Product 1

HCID 220188842-(2-Azabicyclo[2.2.2]oct-2-yl)-6-nitroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-6-nitroquinoline (5.0 g, 24 mmol, Example 1, Step B), 2-azabicyclo[2.2.2]octane p-toluenesulfonic acid salt (10.2 g, 36 mmol) and sodium bicarbonate (5.1 g, 60 mmol) were mixed in absolute ethanol (100 mL) and then heated at reflux for 24 h. The reaction mixture was cooled to r.t., and the solvent removed under vacuum. The solids were taken up in EtOAc (750 mL). The mixture was transferred to a separatory funnel washed with water (3×100 mL) then brine (100 mL). The organic layer was dried over sodium sulfate, filtered and the solvent removed under vacuum to afford the product as a yellow solid, MS: m/z 284 (MH+) which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. customthe solvent removed under vacuum
  4. customThe mixture was transferred to a separatory funnel
  5. washwashed with water (3×100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-a3165b7ee2534a77974b2be0553c8d96
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Reaction notes

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