3-Nitrobenzaldehyde → HCID 178526624, compound

HRID 1036971Notes

Reaction equation

HRID 1036971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O)([O-:11])=[O:10]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[N:8]=[CH:15]/[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 78124-Chloroaniline

Product 1

HCID 178526624HCID 178526624, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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. temperatureThe resulting solution was heated
  2. temperatureto reflux with a dean-stark trap for 3 h
  3. customThe toluene was removed
  4. customthe residue was collect

Sources & evidence

ORD record
ord-e83110cd04754d3e87e3b6f50c306644
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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