Ammonium Hydroxide → HCID 13338836, compound

HRID 1285499Notes

Reaction equation

HRID 1285499 reaction equation
[F:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[C:14]2S)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[OH-].[NH4+]>[Ni].C(O)C>[F:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 178422903HCID 178422903, compound

Product 1

HCID 13338836HCID 13338836, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 30 g (0.115 mmole) of 6-fluoro-2-methyl-5-(2-mercaptoimidazol-1-yl)quinoline, 60 ml of ammonium hydroxide and 300 ml of 60% aqueous ethanol was heated to 50°-55° C. and 201 g of Raney nickel was added. The mixture was heated to reflux and maintained at reflux for four hours, at which time it was filtered. The residue was washed with hot aqueous ethanol, and the washings and filtrate were combined and evaporated to provide 6-fluoro-5-(imidazol-1-yl)-2-methylquinoline as a yellow solid.

Workup

  1. temperaturewas heated to 50°-55° C.
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for four hours, at which time it
  6. filtrationwas filtered
  7. washThe residue was washed with hot aqueous ethanol
  8. customevaporated

Sources & evidence

ORD record
ord-452945b3ce67476098f8ccee6d7d6745
Source dataset
uspto-grants-1986_01
Patent number
US04567269

Reaction notes

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