3-Cyclohexylcarbonyl-4-chloro-8-methoxyquinoline → 3-Cyclohexylcarbonyl-4-(2-methylphenylamino)-8-methoxyquinoline

HRID 1382269Notes

Reaction equation

HRID 1382269 reaction equation
[CH:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2Cl)=[CH:16][CH:15]=[CH:14][C:13]=3[O:20][CH3:21])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCOCC1.NC1C(C)=CC=CC=1>[CH:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[O:20][CH3:21])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 117225423-Cyclohexylcarbonyl-4-chloro-8-methoxyquinoline

Product 1

HCID 102488463-Cyclohexylcarbonyl-4-(2-methylphenylamino)-8-methoxyquinolineYield 18.2%

Reagents, catalysts & solvents 2

HCID 7242O-ToluidineSolventHCID 312751,4-DioxaneSolvent

Procedure

3-cyclohexylcarbonyl-4-chloro-8-methoxyquinoline (5.0 g, 0.017 mol) was heated under reflux in a mixture of 1,4-dioxan (50 ml) and o-toluidine (2.0 ml) for 2 hours. The reaction mixture was evaporated and the residue dissolved in dichloromethane, washed with sodium hydrogen carbonate solution and brine. The organic solution was dried, evaporated and chromatographed (silica gel, dichloromethane) to affort an oil, which on trituration with hexane-ether gave 3-cyclohexylcarbonyl-4-(2-methylphenylamino)-8-methoxyquinoline as yellow crystals (0.58 g, 9.4%) m.p. 115°-7° C.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with sodium hydrogen carbonate solution and brine
  4. customThe organic solution was dried
  5. customevaporated
  6. customchromatographed (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-57226a1bcbd147a793daa544ce16ad2b
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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