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

HRID 1382274Notes

Reaction equation

HRID 1382274 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 dissovled 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 (silica 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. washwashed with dilute hydrochloric acid, sodium hydrogen carbonate solution, water and brine
  3. customThe organic solution was dried
  4. customevaporated to an oil which
  5. customwas chromatographed (silica gel, 1% methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-0c984246de4c4b89934570c99b01f5b4
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

Loading…