Isobutylene → HCID 67290202, compound

HRID 1036961Notes

Reaction equation

HRID 1036961 reaction equation
[CH2:1]=[C:2]([CH3:4])[CH3:3].[N+:5]([C:8]1[CH:9]=[C:10](/[CH:14]=[N:15]/[C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6]>C(#N)C.B(F)(F)F.CCOCC>[CH3:1][C:2]1([CH3:4])[C:17]2[C:16](=[CH:23][CH:22]=[C:19]([C:20]#[N:21])[CH:18]=2)[NH:15][CH:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 8255IsobutyleneHCID 178510045HCID 178510045, compound

Product 1

HCID 67290202HCID 67290202, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a small reactor, isobutene (100 mL, 1.19 mol) was added to a mixture of boron trifluoride etherate (12 mL, 0.96 mmol) and 4-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-benzonitrile (30 g, 0.12 mol) in dry acetonitrile (300 mL), sealed. The resultant mixture was allowed to stir at 30° C. for 10 h. The reaction mixture was washed by brine and dried over anhydrous sodium sulfate. It was filtered and concentrated to provide the crude product (30 g). The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1) to afford 4,4-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonitrile as yellow solid (10.2 g, yield: 27.8%).

Workup

  1. customsealed
  2. washThe reaction mixture was washed by brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationIt was filtered
  5. concentrationconcentrated
  6. customto provide the crude product (30 g)
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-d9f45ed871394b2380e3458ef0e85b1d
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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