p-Fluoronitrobenzene → HCID 58596125, compound

HRID 2114526Notes

Reaction equation

HRID 2114526 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21].C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[CH2:22]([CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][O:15][CH2:14][CH2:13][CH2:12][NH:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[CH3:23]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 214993-((2-Ethylhexyl)oxy)propylamine

Product 1

HCID 58596125HCID 58596125, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

2 g of para-fluoronitrobenzene was added to a solution of 20 ml of N-methylpyrrolidinone, 3.19 g of 2-ethylhexyl 3-aminopropyl ether and 2.35 g of K2CO3. The reaction medium was heated at 60° C. for 10 hours and, after it was cooled to room temperature, poured into a water+ice mixture. The resulting medium was extracted with ethyl acetate, and the organic phase was then concentrated by evaporating under vacuum. 2.73 g of N-[2-(3-ethylheptyloxy)ethyl]-4-nitro-1-aminobenzene (9) were obtained.

Workup

  1. temperatureafter it was cooled to room temperature
  2. extractionThe resulting medium was extracted with ethyl acetate
  3. concentrationthe organic phase was then concentrated
  4. customby evaporating under vacuum

Sources & evidence

ORD record
ord-ab46cfd530364570ac355974039fe473
Source dataset
uspto-grants-2008_10
Patent number
US07435267B2

Reaction notes

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