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

HRID 248399노트

반응식

HRID 248399 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4da3aa9301f2452fb4f12336cc0f127f
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210092

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