Boron trifluoride etherate → 4,4-Dimethyl-2-(3-nitro-phenyl)-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline

HRID 1036938Notes

Reaction equation

HRID 1036938 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[N:11]/[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:22]=[C:23]([CH3:25])[CH3:24].B(F)(F)F.CCOCC>C(#N)C>[CH3:22][C:23]1([CH3:25])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[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)[CH2:24]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 178526623HCID 178526623, compound

Product 1

HCID 672891004,4-Dimethyl-2-(3-nitro-phenyl)-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolineYield 27.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [1-(3-nitro-phenyl)-meth-(E)-ylidene]-(4-trifluoromethyl-phenyl)-amine (18.2 g of crude, 62.1 mmol), isobutene (52 mL, 620.6 mmol) and boron trifluoride etherate (1.6 mL, 12.4 mmol) in acetonitrile in a hydrogenated kettle was stirred for two days at room temperature. The solution was evaporated in vacuo and the residue was crystallized by treating with ethyl acetate to give 5.9 g of 4,4-Dimethyl-2-(3-nitro-phenyl)-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (yield: 27.1%).

Workup

  1. customThe solution was evaporated in vacuo
  2. customthe residue was crystallized
  3. additionby treating with ethyl acetate

Sources & evidence

ORD record
ord-f9760690652a43cc9e892f19e45fa825
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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