HCID 22395292, compound → HCID 22395290, compound

HRID 1071839Notes

Reaction equation

HRID 1071839 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:18]=[C:17]([NH:19]C(=O)C)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:18]=[C:17]([NH2:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 22395292HCID 22395292, compound

Product 1

HCID 22395290HCID 22395290, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of N-{2-[(E)-2-phenylethenyl]-4-quinolinyl}acetamide (1.00 g, 3.5 mmol) in 6 N hydrochloric acid (10 mL) was stirred at reflux for 4 h. After cooling to ambient temperature and stirring for 18 h, the solid was collected by filtration. The solid was treated with 10% ammonium hydroxide solution (60 mL) by stirring at ambient temperature overnight, then extracted with ethyl acetate (30 mL). The ethyl acetate layer was separated, washed with water (50 mL), brine (20 mL), dried over Na2SO4, filtered, and the solvent remove in vacuo to provide the title compound as a yellow-orange solid (0.72 g, 84%). MS (API+): M+1: 247 (100%); 1H NMR (300 MHz, DMSO-d6) d 6.79 (br s, 2H, exchangeable), 6.81 (s, 1H), 7.26 (d, J=16.2 Hz, 1H), 7.30-7.46 (m, 4H), 7.55-7.61 (m, 1H), 7.62 (d,J=16.2 Hz, 1H), 7.67-7.73 (m, 2H), 7.77 (d, J=8.4 Hz, 1H), 8.12 (d, J=8.5 Hz, 1H).

Workup

  1. temperatureat reflux for 4 h
  2. stirringstirring for 18 h
  3. filtrationthe solid was collected by filtration
  4. additionThe solid was treated with 10% ammonium hydroxide solution (60 mL)
  5. stirringby stirring at ambient temperature overnight
  6. extractionextracted with ethyl acetate (30 mL)
  7. customThe ethyl acetate layer was separated
  8. washwashed with water (50 mL), brine (20 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe solvent remove in vacuo

Sources & evidence

ORD record
ord-ea035814c4ea432690db522c870952cd
Source dataset
uspto-grants-2005_06
Patent number
US06906193B2

Reaction notes

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