2-Butyrylamino-4-methyl-3-nitropyridine → 7-Methyl-2-propyl-1H-imidazo[4,5-b]pyridine

HRID 248399

反応式

HRID 248399 の反応式
[C:1]([NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[C:11]([CH3:16])[CH:10]=[CH:9][N:8]=1)(=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.C(O)C.[Fe]>[CH3:16][C:11]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:6][C:1]([CH2:2][CH2:3][CH3:4])=[N:13][C:12]=12

参加物

5

反応物 1

HCID 214642392-Butyrylamino-4-methyl-3-nitropyridine

生成物 1

HCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridine収率 65.5%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

A solution of 2-butyrylamino-4-methyl-3-nitropyridine (7.0 g) and iron powder (17.5 g) in a mixture of acetic acid (14 ml) and ethanol (100 ml) was stirred at 90° C. for 3 hours under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was filtered through Celite and the filtrate was evaporated in vacuo. Ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue until pH 7~8 and the resulting suspension was filtered through Celite. The organic layer of the filtrate was separated, washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified with silica gel column chromatography (eluent:ethyl acetate) to give 7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine (3.6 g).

後処理

  1. temperatureAfter being cooled to room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. customthe filtrate was evaporated in vacuo
  4. additionEthyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue until pH 7~8
  5. filtrationthe resulting suspension was filtered through Celite
  6. customThe organic layer of the filtrate was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated in vacuo
  10. customthe residue was purified with silica gel column chromatography (eluent:ethyl acetate)

出典と根拠

ORDレコード
ord-4da3aa9301f2452fb4f12336cc0f127f
出典データセット
uspto-grants-1993_05
特許番号
US05210092

関連ノート

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