p-Fluoronitrobenzene → HCID 57841523, compound

HRID 734159Notes

Reaction equation

HRID 734159 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CN1CCCC1=O.[OH:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][OH:27])[CH2:22][CH2:23][NH2:24]>C(N(CC)CC)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][OH:27])[CH2:20][CH2:19][OH:18])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 98535N,N-Bis(2-hydroxyethyl)ethylenediamine

Product 1

HCID 57841523HCID 57841523, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

5 g of para-fluoronitrobenzene were added to a solution of 60 ml of N-methylpyrrolidinone, 6.29 g of N,N-bis(2-hydroxyethyl)ethylenediamine, and 4.3 g of triethylamine. The reaction medium was heated at 60° C. for 15 hours and, after cooling to room temperature, was poured into a water/ice mixture. A yellow precipitate formed, which was filtered off, reslurried in water, and then dried over P2O5. 7.5 g of 2-[[2-(4-nitrophenylamino)ethyl]-(2-hydroxyethyl)amino]ethanol (19) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. customA yellow precipitate formed
  3. filtrationwhich was filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-33cbf98ae62249329afc2ed27ab5cf2d
Source dataset
uspto-grants-2009_09
Patent number
US07591860B2

Reaction notes

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