3-Butyryl-4-chloro-8-methoxyquinoline → HCID 14989684, compound

HRID 728549Notes

Reaction equation

HRID 728549 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[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:19][C:20]1[S:21][CH:22]=[CH:23][C:24]=1[CH3:25]>O1CCOCC1.ClCCl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[S:21][CH:22]=[CH:23][C:24]=1[CH3:25])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 117775673-Butyryl-4-chloro-8-methoxyquinolineHCID 145364363-Methylthiophen-2-amine

Product 1

HCID 14989684HCID 14989684, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (3.6 g, 0.0137 mol) and 2-amino-3-methylthiophene (3.4 g, 0.03 mol) in 1,4 dioxan (30 ml) under a nitrogen atmosphere were stirred at room temperature for 20 hours. The solvent was evaporated under reduced pressure to give an oil. The oil was taken up in dichloromethane and extracted with 2N hydrochloric acid (3×100ml). The dichloromethane extracts were then washed with sodium carbonate solution (100 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a solid. The solid was purified by flash chromatography using a gradient elution of dichloromethane/methanol (0-5%, 500 ml). The fractions containing the product were combined and evaporated under reduced pressure to give a solid, (1.94 g), m.p. 130°-132°. Recrystallization from ethyl acetate gave the title compound, (1.7 g), m.p. 132°-133°.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give an oil
  3. extractionextracted with 2N hydrochloric acid (3×100ml)
  4. washThe dichloromethane extracts were then washed with sodium carbonate solution (100 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give a solid
  9. customThe solid was purified by flash chromatography
  10. washa gradient elution of dichloromethane/methanol (0-5%, 500 ml)
  11. additionThe fractions containing the product
  12. customevaporated under reduced pressure
  13. customto give a solid, (1.94 g), m.p. 130°-132°
  14. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d6b2990135504790a9e44904127027a7
Source dataset
uspto-grants-1991_09
Patent number
US05049567

Reaction notes

Loading…