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

HRID 1382326Notes

Reaction equation

HRID 1382326 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1Cl)=[CH:16][CH:15]=[CH:14][C:13]=2[O:20][CH3:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C:23]1[C:24]([CH3:29])=[CH:25][CH:26]=[CH:27][CH:28]=1>O1CCOCC1>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[CH:16][CH:15]=[CH:14][C:13]=2[O:20][CH3:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 100860183-Benzoyl-4-chloro-8-methoxyquinoline

Product 1

HCID 99991043-Benzoyl-4-(2-methylphenylamino)-8-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Benzoyl-4-chloro-8-methoxyquinoline (3.0 g, 0.01 mol) was heated under reflux in 1,4-dioxan (100 ml) with o-toluidine (5.0 ml) for 1 hour. The solvent was evaporated and the residue was dissolved in dichloromethane, and washed with dilute hydrochloric acid, sodium hydrogen carbonate solution, water and brine. The organic solution was dried and evaporated to an oil which was chromatographed (silic gel, 1% methanolic ammonia in dichloromethane). 3-Benzoyl-4-(2-methylphenylamino)-8-methoxyquinoline was isolated as crystals (0.95 g, 25.8%) from ether/hexane, m.p. 128-130.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with dilute hydrochloric acid, sodium hydrogen carbonate solution, water and brine
  4. customThe organic solution was dried
  5. customevaporated to an oil which
  6. customwas chromatographed (silic gel, 1% methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-00b2a9a0a4794be79ac99a5c3599e7e0
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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