p-Fluoronitrobenzene → HCID 23104380, compound

HRID 2114524Notes

Reaction equation

HRID 2114524 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]([O:14][CH2:15][CH2:16][NH2:17])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[CH:11]([O:14][CH2:15][CH2:16][NH:17][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 5338662-(Propan-2-yloxy)ethan-1-amine

Product 1

HCID 23104380HCID 23104380, compoundYield 80.9%

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 (NMP), 1.75 g of 2-aminoethyl isopropyl ether and 2.35 g of K2CO3. The reaction medium was heated at 60° C. for 8 hours and, after cooling to room temperature, was poured into a water+ice mixture. A yellow precipitate formed and was filtered off. The precipitate was reslurried in water and then dried over P2O5.2.57 g of N-(2-isopropoxyethyl)-4-nitro-1-aminobenzene (7) were obtained.

Workup

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

Sources & evidence

ORD record
ord-9350af3d5eb54f9ea306a1c04e619307
Source dataset
uspto-grants-2008_10
Patent number
US07435267B2

Reaction notes

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