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

HRID 6799

反応式

HRID 6799 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a3165b7ee2534a77974b2be0553c8d96
出典データセット
uspto-grants-2006_08
特許番号
US07084156B2

関連ノート

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