p-Fluoronitrobenzene → HCID 60698016, compound

HRID 1759758Notes

Reaction equation

HRID 1759758 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C=O)C>[CH:1]([NH:4][CH2:5][CH2:6][NH:7][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 88098N-Isopropylethylenediamine

Product 1

HCID 60698016HCID 60698016, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N-Isopropylethylenediamine (4.87 ml, 39.0 mmol) and potassium carbonate (6.37 g, 46.0 mmol) were added to a solution of 4-fluoronitrobenzene (5.0 g, 35.0 mmol) in DMF (50 ml) and the mixture was heated at 70° C. for 3 hours under a nitrogen atmosphere. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was dissolved in ethyl acetate (300 ml) and the solution was washed with water (3×100 ml) and saturated sodium chloride (50 ml) and dried. The solvent was removed by evaporation to give the product as an orange oil which crystallised on standing (7.55 g, 95%). NMR: 1.0 (d, 6H), 1.7 (m, 1H), 2.7 (m, 3H), 3.2 (m, 1H), 6.6 (m, 2H), 7.1 (m, 1H), 8.0 (m, 2H); MS (MH+): 224.

Workup

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (300 ml)
  4. washthe solution was washed with water (3×100 ml) and saturated sodium chloride (50 ml)
  5. customdried
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-bb8c4f0c3b6a44a1b9d68f59cf9fdddc
Source dataset
uspto-grants-2005_01
Patent number
US06838464B2

Reaction notes

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