HCID 178524696, compound → HCID 66629888, compound

HRID 1942924Notes

Reaction equation

HRID 1942924 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:13]1[O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2](=[O:1])[CH2:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12]1

Participants

3

Reactant 1

HCID 178524696HCID 178524696, compound

Product 1

HCID 66629888HCID 66629888, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A suspension of 4-hydroxy-6,7-methylenedioxy-3-quinolinecarboxylic acid (30 g, 0.129 mol) in diphenyl ether (320 mL) was heated to reflux with vigorous stirring. The reaction was carefully monitored until it became clear, about 1.5 h, and then immediately removed from heat. By this time all of the starting material had dissolved but a black tarry residue remained. The solution was decanted and cooled, allowing the product to precipitate. This material was filtered and washed with ethyl ether to remove all traces of phenyl ether. A second crop was obtained by vigorously washing the tarry residue with ethanol (16×250 mL), filtering and evaporating the ethanol, and rinsing the material with ethyl ether. The total yield was 14.9 g as a pale yellow solid, in 61%; mp 285-289° C. (lit.221 in mp 276° C.); 1H NMR (DMSO-d6) δ 5.95 (d, 1H, J=7.3), 6.13 (s, 2H), 6.97 (s, 1H), 7.38 (s, 1H), 7.77 (d, 1H, J=7.3); 13C NMR (DMSO-d6) δ 97.5, 102.1, 102.6, 108.7, 119.4, 122.0, 130.8, 138.7, 145.8, 151.7.

Workup

  1. temperaturewas heated
  2. temperatureto reflux with vigorous stirring
  3. customimmediately removed
  4. temperaturefrom heat
  5. dissolutionBy this time all of the starting material had dissolved
  6. customThe solution was decanted
  7. temperaturecooled
  8. customto precipitate
  9. filtrationThis material was filtered
  10. washwashed with ethyl ether
  11. customto remove all traces of phenyl ether
  12. customA second crop was obtained
  13. washby vigorously washing the tarry residue with ethanol (16×250 mL)
  14. filtrationfiltering
  15. customevaporating the ethanol
  16. washrinsing the material with ethyl ether

Sources & evidence

ORD record
ord-53af6f992760459f93a7f029e63872c6
Source dataset
uspto-grants-2013_03
Patent number
US08389721B2

Reaction notes

Loading…