Ethyl Acetate → HCID 79458467, compound

HRID 2284686Notes

Reaction equation

HRID 2284686 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH:17]1([NH2:24])[CH2:22][CH2:21][CH2:20][CH:19]([NH2:23])[CH2:18]1.C(OCC)(=O)C>C(#N)C.O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:23][CH:19]1[CH2:20][CH2:21][CH2:22][CH:17]([NH2:24])[CH2:18]1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 188141,3-CyclohexanediamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 79458467HCID 79458467, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-fluoronitrobenzene (197 mg) and potassium carbonate (193 mg) in acetonitrile (4 mL), 1,3-cyclohexanediamine (480 mg) was added at room temperature, and the mixture was stirred for 10 hours and 30 minutes under reflux by heating. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 80% ethyl acetate in methanol) to obtain N1-(2-nitrophenyl)cyclohexane-1,3-diamine (C41, 162 mg).

Workup

  1. additionwas added at room temperature
  2. temperatureunder reflux
  3. temperatureby heating
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 80% ethyl acetate in methanol)

Sources & evidence

ORD record
ord-4320526ea24a4385aec9c729a7216a17
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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