Hydrogen Peroxide → HCID 178498485, compound

HRID 328716Notes

Reaction equation

HRID 328716 reaction equation
[Br:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]([OH:16])[C:6]=2[C:5]2[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[S:19](=[O:20])[C:4]=2[CH:3]=1.[OH:25]O>C(O)(=O)C>[Br:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]([OH:16])[C:6]=2[C:5]2[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[S:19](=[O:25])(=[O:20])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 178498484HCID 178498484, compound

Product 1

HCID 178498485HCID 178498485, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.6 g. of methyl 5-bromo-1-hydroxy[1]benzothieno[3,2-f]quinoline-3-carboxylate-7-oxide in glacial acetic acid is added excess 30 percent hydrogen peroxide. The mixture is heated to its reflux temperature and maintained at reflux for one hour, then allowed to cool. The precipitate is separated by filtration to give methyl 5-bromo-1-hydroxy[1]-benzothieno[3,2-f]quinoline-3-carboxylate-7,7-dioxide, crude m.p. 240°-260° C. Infrared spectral analysis is consistent with the assigned structure. This ester is hydrolyzed using the method of Example 32 (or 33) to provide 5-bromo-1-hydroxy[1]-benzothieno[3,2-f]quinoline-3-carboxylic acid-7,7-dioxide, m.p. 283°-285° C. (dec.). Analysis: Calculated for C16H8BrNO4S. 3/4 H2O: %C, 45.8; %H, 2.3; %N, 3.4; Found: %C, 46.1; %H, 2.2; %N, 3.4.

Workup

  1. temperatureThe mixture is heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for one hour
  5. temperatureto cool
  6. customThe precipitate is separated by filtration

Sources & evidence

ORD record
ord-e91d549481c44b42bcc4d0be1cf0216d
Source dataset
uspto-grants-1977_04
Patent number
US04018780

Reaction notes

Loading…