O-Toluidine → 3-Butyryl-4-(2-methylphenylamino)-8-phthalimidoquinoline

HRID 1090671Notes

Reaction equation

HRID 1090671 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[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:28][C:29]1[C:30]([CH3:35])=[CH:31][CH:32]=[CH:33][CH:34]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])=[CH:13][CH:12]=[CH:11][C:10]=2[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 100910853-Butyryl-4-chloro-8-phthalimidoquinoline

Product 1

HCID 104788903-Butyryl-4-(2-methylphenylamino)-8-phthalimidoquinolineYield 58.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-butyryl-4-chloro-8-phthalimidoquinoline (61.6 g, 0.16 moles) and o-toluidine (20 ml, 0.19 mol) was heated under reflux in 1,4-dioxan (300 ml) for 3 hours. The solvent was evaporated and the residue was dissolved in chloroform, washed with dil. ammonia solution and brine. The organic solution was dried (anhyd. MgSO4) filtered and evaporated to a dark oil which crystallized on standing to give 3-butyryl-4-(2-methylphenylamino)-8-phthalimidoquinoline (42 g, 58.3%), m.p. b 170°-2° C.

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with dil. ammonia solution and brine
  5. dry with materialThe organic solution was dried (anhyd. MgSO4)
  6. filtrationfiltered
  7. customevaporated to a dark oil which
  8. customcrystallized

Sources & evidence

ORD record
ord-848098239eba49f383b04aef34a39fe6
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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