Triethylamine → HCID 22458611, compound

HRID 2185461Notes

Reaction equation

HRID 2185461 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>[Pd].C(O)C.ClCCl.[O-2].[Mn+2]>[CH2:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 8471TriethylamineHCID 22458564HCID 22458564, compound

Product 1

HCID 22458611HCID 22458611, compoundYield 74.7%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 160959Manganese oxideCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of crude ethyl 6-benzyl-4-chloroquinoline-3-carboxylate (B, 2.77 g), 10% palladium on activated carbon (0.28 g) and triethylamine (2.8 mL) in ethanol (30 mL) was stirred under a hydrogen atmosphere at room temperature for 19 hr. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was diluted with water and extracted with dichloromethane. The organic layer was washed with 10% citric acid, saturated sodium hydrogen carbonate, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane then dichloromethane:ethyl acetate=50:1 to 20:1, v/v) to afford overreduced compound. The hydroquinoline was dissolved in dichloromethane (30 mL) and activated manganese oxide (0.9 g) was added to the solution. After stirring at room temperature for 20 hr, the mixture was filtered through celite and concentrated in vacuo to afford the title compound (1.85 g) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.45 (t, J=6.8 Hz, 3H), 4.19 (s, 2H), 4.47 (q, J=6.8 Hz, 2H), 7.20-7.38 (m, 5H), 7.63-7.72 (m, 2H), 8.97 (d, J=8.8 Hz, 1H), 8.76 (d, J=1.5 Hz, 1H), and 9.39 (d, J=1.5 Hz, 1H); mass spectrum (EI+) m/e 291 (M+); (FAB+) m/e 292 (M+1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with 10% citric acid, saturated sodium hydrogen carbonate, and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (dichloromethane
  9. customdichloromethane:ethyl acetate=50:1 to 20:1, v/v) to afford overreduced compound
  10. stirringAfter stirring at room temperature for 20 hr
  11. filtrationthe mixture was filtered through celite and
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94c13a6d9a13455c84bdc153adddc8e5
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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