p-Aminoacetophenone → HCID 67529114, compound

HRID 2092936Notes

Reaction equation

HRID 2092936 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH3:12])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 7468p-AminoacetophenoneHCID 10796Cesium carbonateHCID 2318282-Bromo-3-nitrotoluene

Product 1

HCID 67529114HCID 67529114, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalystHCID 1140TolueneSolvent

Procedure

In a flask under an argon atmosphere are consecutively placed 2.16 g of 2-bromo-3-nitrotoluene, 1.69 g of 4-aminoacetophenone (1.25 equivalents), 229 mg of dipalladium trisdibenzylideneacetone (0.025 equivalents), 269 mg of DPEPhos (0.05 equivalents) and 4.07 g of cesium carbonate (1.25 equivalents). The toluene is added at room temperature. The heterogeneous reaction medium is purged with argon and refluxed for hours. After returning to room temperature, water and ethyl acetate are added. After separation of the phases, the organic phase is washed with water and then with a saturated NaCl solution, dried on sodium sulphate, filtered and then dry evaporated. The obtained red oil is purified by chromatography on silica (ethyl acetate/cyclohexane:5/95 to 10/90) in order to provide 2.29 g of the expected compound as a red oil.

Workup

  1. customIn a flask under an argon atmosphere are consecutively placed
  2. customThe heterogeneous reaction medium is purged with argon
  3. temperaturerefluxed for hours
  4. customAfter returning to room temperature
  5. additionwater and ethyl acetate are added
  6. customAfter separation of the phases
  7. washthe organic phase is washed with water
  8. dry with materialwith a saturated NaCl solution, dried on sodium sulphate
  9. filtrationfiltered
  10. customdry
  11. customevaporated
  12. customThe obtained red oil is purified by chromatography on silica (ethyl acetate/cyclohexane:5/95 to 10/90) in order

Sources & evidence

ORD record
ord-130a0250eb0d41399c5e3ea97e92fd58
Source dataset
uspto-grants-2013_05
Patent number
US08440833B2

Reaction notes

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