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

HRID 1955662ノート

反応式

HRID 1955662 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochloride2 回HCID 105834305-nitro-1H-indol-1-amine

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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, dried over anhydrous magnesium sulfate, 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° C. This material was converted to the hydrochloride salt and recrystallized twice from methanol/ether to give 3.5 g of orange needles, m.p. 300°-302° C. (dec.).

後処理

  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 materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to 9 g of dark oil
  10. customThis oil was purified by flash chromatography (silica, ethyl acetate)

出典と根拠

ORDレコード
ord-e3da2d64280f4c6c95cdbfa7b10ad703
出典データセット
uspto-grants-1998_07
特許番号
US05776955

反応ノート

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