3-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester → Ethyl 8-methoxy-4-(4-methoxy-3-thienylamino)quinoline-3-carboxylate

HRID 1084729

Reaction equation

HRID 1084729 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]2Cl.[CH3:19][O:20][C:21]1[C:22]([NH2:26])=[CH:23][S:24][CH:25]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]2[NH:26][C:22]1[C:21]([O:20][CH3:19])=[CH:25][S:24][CH:23]=1

Participants

4

Reactant 2

HCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl esterHCID 149896854-Methoxythiophen-3-amine

Product 1

HCID 14989686Ethyl 8-methoxy-4-(4-methoxy-3-thienylamino)quinoline-3-carboxylateYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 8-methoxy-4-chloroquinoline-3-carboxylate (1.5 g, 0.0056 mol) and 4-methoxy-3-aminothiophene (1.46 g, 0.0112 mol) in 1,4 dioxan (20 ml) were heated under reflux for 4 hours. The solid which had formed was collected by filtration and dried. The solid was dissolved in chloroform, washed with sodium carbonate solution (50 ml), then water, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a yellow solid. Recrystallization from ethyl acetate gave the title compound, (1.53 g) m.p. 176°-178°.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solid which had formed
  3. filtrationwas collected by filtration
  4. customdried
  5. dissolutionThe solid was dissolved in chloroform
  6. washwashed with sodium carbonate solution (50 ml)
  7. dry with materialwater, dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give a yellow solid
  11. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-749dbe78ec7e49cc892975268f9012ca
Source dataset
uspto-grants-1991_04
Patent number
US05006535

Linked notes

Loading…