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

HRID 1955662Notes

Reaction equation

HRID 1955662 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.).

Workup

  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)

Sources & evidence

ORD record
ord-e3da2d64280f4c6c95cdbfa7b10ad703
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

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