O-Toluidine → 3-Isobutyryl-4-(2-methylphenylamino)-8-methoxyquinoline

HRID 1382282Notes

Reaction equation

HRID 1382282 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:19][C:20]1[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>O1CCOCC1.CCOCC>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 7242O-ToluidineHCID 100841433-Isobutyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 103148303-Isobutyryl-4-(2-methylphenylamino)-8-methoxyquinolineYield 19.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

3-isobutyryl-4-chloro-8-methoxyquinoline (6.0 g, 0.022 mol) and o-toluidine (6 ml, 0.055 mol) were heated in 1,4-dioxan (100 ml) for 45 minutes. The solvent was evaporated and the residue was dissolved in dichloromethane, washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and brine. The solution was dried and evaporated to an oil, which was chromatographed (silica gel, dichloromethane) to afford a yellow oil. Trituration in ether gave yellow crystals of 3-isobutyryl-4-(2-methylphenylamino)-8-methoxyquinoline (1.41 g, 18.3%), m.p. 116°-8°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with dilute hydrochloric acid, sodium hydrogen carbonate solution and brine
  4. customThe solution was dried
  5. customevaporated to an oil, which
  6. customwas chromatographed (silica gel, dichloromethane)
  7. customto afford a yellow oil

Sources & evidence

ORD record
ord-0176528adeeb46e2ae0b675e3fa7c360
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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