Imidazole → 3-Amino-4,5-diethoxycarbonyl-6-(imidazol-1-yl)-2-phenylpyridine

HRID 37498

반응식

HRID 37498 반응식
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-])=O)=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1>C(Cl)(Cl)Cl>[NH2:18][C:5]1[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:3][C:2]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

4

반응물 2

HCID 795ImidazoleHCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

생성물 1

HCID 152897003-Amino-4,5-diethoxycarbonyl-6-(imidazol-1-yl)-2-phenylpyridine수율 89.8%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 0.379 g of 2-chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine, 0.21 g of imidazole and 15 ml of chloroform was heated under reflux for 8 hours. After the reaction mixture was concentrated, the residue was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate. After the solvent was distilled off, 5 ml of acetic acid and 0.5 g of reduced iron were added to the residue, and the mixture was stirred at room temperature for 4 hours. After an aqueous solution of sodium hydrogencarbonate was added for neutralization, extraction with ethyl acetate was conducted. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate, followed by filtration with a small amount of silica gel. The filtrate was concentrated under reduced pressure, to give 0.342 g of the title compound as a yellow oily substance.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
  7. distillationAfter the solvent was distilled off
  8. addition5 ml of acetic acid and 0.5 g of reduced iron were added to the residue
  9. additionAfter an aqueous solution of sodium hydrogencarbonate was added for neutralization, extraction with ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
  12. filtrationfollowed by filtration with a small amount of silica gel
  13. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-78b21301283c45709220707c2c207948
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420275

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