Pyridine → N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-N-(4-nitrophenyl)amine

HRID 1391399Notes

Reaction equation

HRID 1391399 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:17]([NH2:31])[CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH2:29][NH2:30]>O>[NH2:30][CH2:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][CH2:17][NH:31][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9590p-FluoronitrobenzeneHCID 20239Diethylene glycol bis(3-aminopropyl) ether

Product 1

HCID 56652140N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-N-(4-nitrophenyl)amineYield 52.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1.41 g (0.01 mol) of 1-fluoro-4-nitrobenzene and 1.62 ml (0.02 mol) of pyridine were introduced into a three-necked flask under nitrogen. 8.75 ml (0.04 mol) of 4,7,10-trioxatridecane-1,13-diamine were added dropwise with stirring. The mixture was heated to 70° C. After reaction for 24 hours, the reaction mixture was cooled and 40 ml of distilled water were then added with vigorous stirring. Next, the reaction mixture was extracted with dichloromethane, washed twice with water, dried over MgSO4 and then evaporated under vacuum. The crude product, isolated in the form of a yellow oil comprising about 90% of expected mono-nitro derivative, was purified on a column of silica, eluting with ethyl acetate (to separate out the dinitro derivative), and then with methanol (to recover the expected mono-nitro derivative). 1.8 g of expected product (19) were obtained in the form of a dark yellow oil.

Workup

  1. customAfter reaction for 24 hours
  2. temperaturethe reaction mixture was cooled
  3. extractionNext, the reaction mixture was extracted with dichloromethane
  4. washwashed twice with water
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum
  7. customThe crude product, isolated in the form of a yellow oil
  8. customwas purified on a column of silica
  9. washeluting with ethyl acetate (
  10. customto separate out the dinitro derivative), and then with methanol (
  11. customto recover the expected mono-nitro derivative)

Sources & evidence

ORD record
ord-f2eccf9ac81947d192202696038a900a
Source dataset
uspto-grants-2008_03
Patent number
US07338536B2

Reaction notes

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