Potassium Carbonate → But-3-enyl-(3-fluoro-6-nitro-2-vinylphenyl)amine

HRID 243205Notes

Reaction equation

HRID 243205 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[C:3]=1[CH:12]=[CH2:13].Cl.[CH2:15]([NH2:19])[CH2:16][CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:15]([NH:19][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH:12]=[CH2:13])[CH2:16][CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12363007But-3-en-1-amine hydrochlorideHCID 681573311,3-Difluoro-4-nitro-2-vinylbenzene

Product 1

HCID 68157662But-3-enyl-(3-fluoro-6-nitro-2-vinylphenyl)amineYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 1,3-difluoro-4-nitro-2-vinylbenzene (389 mg, 2.1 mmol) in DMF (8 mL) was added 3-butenylamine hydrochloride (248 mg, 2.31 mmol) and potassium carbonate (0.87 g, 6.3 mmol). The reaction mixture was stirred at RT for 2 h, and then partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 2-4% EtOAc in cyclohexane) affording the title compound as an orange oil (327.6 mg, 66%). LCMS (Method B): RT 4.27 min [M+H]+ 237

Workup

  1. custompartitioned between water and EtOAc
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic layers were washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, eluant 2-4% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-55c9928c8d3e4f47964a77c8ad422d8a
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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