Boron trifluoride etherate → HCID 67290448, compound

HRID 1036950Notes

Reaction equation

HRID 1036950 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[N:11]/[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].B(F)(F)F.CCOCC.[CH2:28]=[C:29]([CH3:31])[CH3:30]>C(#N)C>[CH3:28][C:29]1([CH3:31])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=2)[NH:11][CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:30]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 178426385HCID 178426385, compound

Product 1

HCID 67290448HCID 67290448, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 2000 mL of autoclave was charged with [1-(3-nitro-phenyl)-meth-(E)-ylidene]-p-tolyl-amine (44.5 g, 0.185 mmol), acetonitrile (500 mL), boron trifluoride etherate (30 mL). The mixture was cooled with liquid nitrogen, and then isobutene was added quickly. The resultant mixture was stirred at room temperature for 60 h. The reaction mixture was washed with brine, water, dried over magnesium sulfate, concentrated. The residue was washed with ethyl acetate and the desired 4,4,6-trimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline was obtained by filtration (53 g).

Workup

  1. temperatureThe mixture was cooled with liquid nitrogen
  2. washThe reaction mixture was washed with brine, water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-d142425e72fc41eca60fb5891b859a96
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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