Acetonitrile → HCID 67290257, compound

HRID 1036972Notes

Reaction equation

HRID 1036972 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[N:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[CH:4][CH:3]=1.[CH2:19]=[C:20]([CH3:22])[CH3:21].B(F)(F)F.CCOCC.C(#N)C>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:19][C:20]2([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 178526624HCID 178526624, compound

Product 1

HCID 67290257HCID 67290257, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 4-chloro-phenylamine (12.8 g 100 mmol) and 3-nitro-benzaldehyde (15.1 g, 100 mmol) was added 100 mL of toluene. The resulting solution was heated to reflux with a dean-stark trap for 3 h. The toluene was removed and the residue was collect to afford (4-chloro-phenyl)-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amine as yellow solid (26.5 g, yield: 95%). (4-Chloro-phenyl)-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amine (10.0 g, 36.5 mmol), isobutene (31 ml, 365.4 mmol, 10 g), boron trifluoride etherate (1.98 ml, 7.31 mmol) and acetonitrile (40 ml) were added into a autoclave and was stirred at room temperature for 72 h. Brine was added and the organic layer was separated, dried and concentrated to afford 6-chloro-4,4-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline as yellow solid (8.7 g, yield: 73%).

Workup

  1. customthe organic layer was separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-595e4a3db783414e88d2628f99fc5070
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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