Boron trifluoride etherate → HCID 67291102, compound

HRID 1036920Notes

Reaction equation

HRID 1036920 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH:6]=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)([O-:3])=[O:2].B(F)(F)F.CCOCC.[CH2:31]=[C:32]([CH3:34])[CH3:33]>C(#N)C>[CH3:31][C:32]1([CH3:34])[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([C:14]([F:15])([F:16])[F:17])[CH:10]=2)[NH:7][CH:6]([C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:33]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 67291521N-(2-nitrobenzylidene)-4-(trifluoromethyl)aniline

Product 1

HCID 67291102HCID 67291102, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of N-(2-nitrobenzylidene)-4-(trifluoromethyl)aniline (2.7 g, 9.18 mmol) and Borontrifluoride etherate (289 μL) in anhydrous acetonitrile was added isobutene (16 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-dimethyl-2-(2-nitrophenyl)-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline (2.56 g, yield 80%). LC/MS m/e obsd. (ESI+) [(M+H)+] 351.1.

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-db23e3318caa469ab6eb431317505f96
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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