Boron trifluoride etherate → HCID 67291098, compound

HRID 1036931Notes

Reaction equation

HRID 1036931 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([N:6]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[CH2:28]=[C:29]([CH3:31])[CH3:30]>C(#N)C>[CH3:28][C:29]1([CH3:31])[C:4]2[C:5](=[CH:17][CH:18]=[C:2]([CH3:1])[CH:3]=2)[NH:6][CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:30]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 794913N-(2-Nitrobenzylidene)-P-toluidine

Product 1

HCID 67291098HCID 67291098, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-methyl-N-(2-nitrobenzylidene)aniline (10 g) and boron trifluoride etherate (3 mL) in anhydrous acetonitrile was added isobutene (70 mL, pre-cooled to −78° C.) at ice-bath. After addition, the resulting mixture was stirred at 90° C. in sealed tube overnight. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give 4,4,6-trimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (10.5 g, yield 85.4%). LC/MS m/e obsd. (ESI+) [(M+H)+] 297.2.

Workup

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d257d367a4bd43e1be3c3cdc5c2beace
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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