Pyridine → (+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-(n-4-chlorophenyl)aminoquinoline

HRID 1785888Notes

Reaction equation

HRID 1785888 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH2:19])[CH2:11][C@@H:10]2[CH3:20])=[O:8])=[CH:5][CH:4]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.N1C=CC=CC=1.C(OCC)(=O)C>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:23][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH:19][C:28]3[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=3)[CH2:11][C@@H:10]2[CH3:20])=[O:8])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 742994-Chlorophenylboronic acidHCID 68921648(+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-aminoquinoline

Product 1

HCID 131726427(+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-(n-4-chlorophenyl)aminoquinolineYield 22%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (±)-cis-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-aminoquinoline (423 mg, 1.36 mmol) in DMF (15 mL, dry) was added 4-chlorophenylboronic acid (425 mg, 2.72 mmol), pyridine (322 mg, 330 uL, 4.08 mmol) and copper(II)acetate (494 mg, 2.72 mmol). The heterogeneous green mixture was stirred open to air for 1 h and then warmed to 60° C. and stirred over night (14 h). The mixture was then cooled to rt, poured into rapidly stirred ethyl acetate (150 mL); solids were removed by filtration. The extracts were washed several times with water and then once with brine. The extracts were then dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (100% hexanes to 50/50 hexanes/ethyl acetate gradient) to afford the aniline product (120 mg, 22%) as a yellow oil.

Workup

  1. stirringstirred over night (14 h)
  2. temperatureThe mixture was then cooled to rt
  3. customsolids were removed by filtration
  4. washThe extracts were washed several times with water
  5. dry with materialThe extracts were then dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica gel chromatography (100% hexanes to 50/50 hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-96b71d3e08354fd7bf6e627018cf69a0
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…