Water → 5-Nitro-N-(4-pyridinyl)-1H-indol-1-amine hydrochloride

HRID 1073546노트

반응식

HRID 1073546 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH2:13])[CH:8]=[CH:7]2)([O-:3])=[O:2].Cl.[Cl:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[ClH:15].[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH:13][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochloride2회HCID 105834305-nitro-1H-indol-1-amine

생성물 1

HCID 190724035-Nitro-N-(4-pyridinyl)-1H-indol-1-amine hydrochloride수율 51.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of 5-nitro-1H-indol-1-amine (4.5 g) and 4-chloropyridine hydrochloride (4.5 g) in 175 ml of isopropanol was stirred at reflux for two hours, another equivalent of 4-chloropyridine hydrochloride was added and the mixture was refluxed for two additional hours. The reaction mixture was then cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution, was dried (MgSO4), filtered and concentrated to 9 g of dark oil. This oil was purified by flash chromatography (silica, ethyl acetate) to give 3.8 g of light brown solid, m.p. 183°-184°. This material was converted to the hydrochloride salt and recrystallized twice from methanol/ether to give 3.5 g of orange needles, d 300°-302°.

후처리

  1. temperatureat reflux for two hours
  2. temperaturethe mixture was refluxed for two additional hours
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and saturated sodium chloride solution
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to 9 g of dark oil
  10. customThis oil was purified by flash chromatography (silica, ethyl acetate)

출처 및 근거

ORD 기록
ord-8e33e9295b4847c7888b78472e51a83e
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04970218

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