Nitric Acid → HCID 70224229、化合物

HRID 1384269ノート

反応式

HRID 1384269 の反応式
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[N+:11]([O-:12])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[CH:8][C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+]>>[CH3:5][C:6]1[N+:11]([O-:12])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[C:8]([N+:1]([O-:4])=[O:2])[C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

参加物

4

反応物 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 70224223HCID 70224223、化合物

生成物 1

HCID 70224229HCID 70224229、化合物収率 92.4%

反応条件

温度
90 °C

実験手順

Fuming nitric acid (27.0 ml) was added dropwise to ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (3.10 g, 12.4 mmol) at 0° C., and the mixture was stirred at 90° C. for 2 hours. After cooling, the reaction solution was poured into ice water, mixed with 2 N sodium hydroxide aqueous solution and extracted with chloroform, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=40:1) to obtain the title compound (3.38 g, 92.4%) as pale yellow powder.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washthe thus obtained organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=40:1)

出典と根拠

ORDレコード
ord-e172ef55557049279b148bb2cd118a60
出典データセット
uspto-grants-2001_07
特許番号
US06258829B1

反応ノート

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