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

HRID 1382265Notes

Reaction equation

HRID 1382265 reaction equation
[C:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1Cl)=[CH:15][CH:14]=[CH:13][C:12]=2[O:19][CH3:20])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:21][C:22]1[C:23]([CH3:28])=[CH:24][CH:25]=[CH:26][CH:27]=1>O1CCOCC1>[C:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[CH:15][CH:14]=[CH:13][C:12]=2[O:19][CH3:20])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 101083533-Hexanoyl-4-chloro-8-methoxyquinoline

Product 1

HCID 99987513-Hexanoyl-4-(2-methylphenylamino)-8-methoxyquinolineYield 45.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-hexanoyl-4-chloro-8-methoxyquinoline (5 g, 0.071 mol) and o-toluidine (2 ml, 0.019 mol) were heated under reflux in 1,4-dioxan (50 ml) for 1 hour. The solvent was evaporated and the residue was taken up in dichloromethane, washed with 10% hydrochloric acid, water, sodium hydrogen carbonate solution and brine, dried and evaporated. Trituration with ethyl acetate/ether and recrystallisation from methanol-water gave 3-hexanoyl-4-(2-methylphenylamino)-8-methoxyquinoline as yellow needles (2.53 g, 45.3%), m.p. 94°-6° C.

Workup

  1. customThe solvent was evaporated
  2. washwashed with 10% hydrochloric acid, water, sodium hydrogen carbonate solution and brine
  3. customdried
  4. customevaporated
  5. customTrituration with ethyl acetate/ether and recrystallisation from methanol-water

Sources & evidence

ORD record
ord-ef6447e20896460eb0c001174ff37866
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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